Diastereo- and Enantioselective Syntheses of C ₂-Symmetric 1,n-Diamines by Nucleophilic Addition to Dialdehyde-SAMP-Hydrazones

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

Different protected C ₂-symmetric 1,n-diamines (R,R)- or (S,S)-4 and 8 can be prepared in high diastereo- and enantiomeric purity by nucleophilic 1,2-addition of organocerium reagents to the CN double bond of bis-SAMP-hydrazones (S,S)-2a∠c. The chiral starting materials are readily available by reaction of dialdehydes with the enantiopure hydrazine 1-amino-2-methoxymethylpyrrolidine (SAMP). Reductive NN bond cleavage of the hydrazines (R,R,S,S)- or (S,S,S,S)-3 and 7 afforded the title compounds (de 72∠98%, ee 96∠98%). The novel entry for the asymmetric synthesis of N-protected C ₂-symmetric diamines presented here is highly flexible, as both the distance of the amino functions and the introduced residues R can be varied.

References

• 1 For a recent review, see: Fache F. Schulz E. Tommasino ML. Lemaire M. Chem. Rev.  2000,  100:  2159 
  CrossrefPubMedSearch in Google Scholar
• For reviews see:
• 2a Lucet D. Le Gall T. Mioskowski C. Angew. Chem. Int. Ed.   1998,  37:  2580 ; Angew. Chem. 1998, 110, 2724
  CrossrefPubMedSearch in Google Scholar
• 2b Bennani Y. Hanessian S. Chem. Rev.  1997,  97:  3161 
  CrossrefPubMedSearch in Google Scholar
• For examples see:
• 3a Hanessian S. Delorme D. Beaudoin S. Leblanc Y. J. Am. Chem. Soc.  1984,  106:  5754 
  CrossrefSearch in Google Scholar
• 3b Corey EJ. Pure Appl. Chem.  1990,  62:  1209 ; and literature cited therein
  CrossrefSearch in Google Scholar
• 3c Corey EJ. Kim SS. J. Am. Chem. Soc.  1990,  112:  4976 
  CrossrefSearch in Google Scholar
• 3d Blaszis VJ. Koeller KJ. Spilling CD. Tetrahedron: Asymmetry  1994,  5:  499 
  CrossrefSearch in Google Scholar
• 3e Alexakis A. Mangeney P. Lensen N. Tranchier J.-P. Gosmini R. Raussou S. Pure Appl. Chem.  1996,  68:  531 ; and ref. cited therein
  CrossrefSearch in Google Scholar
• 3f Hanessian S. Andreotti D. Gomtsyan A. J. Am. Chem. Soc.  1995,  117:  10393 
  CrossrefSearch in Google Scholar
• 3g Davies SG. Mortlock AA. Tetrahedron  1993,  49:  4419 
  CrossrefSearch in Google Scholar
• 3h Davies SG. Evans GB. Mortlock AA. Tetrahedron: Asymmetry  1994,  5:  585 
  CrossrefSearch in Google Scholar
• For reviews see also:
• 4a Jacobsen EN. In Catalytic Asymmetric Synthesis   Ojima I. VCH; New York: 1993.  p.159 
  Crossref
• 4b Katsuki T. Coord. Chem. Rev.  1995,  140:  189  For recent examples see:
  CrossrefSearch in Google Scholar
• 4c Fujii A. Hashiguchi S. Uematsu N. Ikariya T. Noyori R. J. Am. Chem. Soc.  1996,  118:  2521 
  CrossrefSearch in Google Scholar
• 4d Nishibayashi Y. Arikawa Y. Ohe K. Uemura S. J. Org. Chem.  1996,  61:  1172 
  CrossrefSearch in Google Scholar
• 4e Ohkuma T. Ooka H. Hashiguchi S. Ikariya T. Noyori R. J. Am. Chem. Soc.  1995,  117:  2675 
  CrossrefSearch in Google Scholar
• 4f Alexakis A. Kanger T. Mangeney P. Rose-Munch R. Perrotey A. Rose E. Tetrahedron: Asymmetry  1995,  6:  2135 
  CrossrefSearch in Google Scholar
• 4g Gamez P. Fache F. Lemaire M. Terahedron: Asymmetry  1995,  6:  705 
  CrossrefSearch in Google Scholar
• 4h Murata K. Ikariya T. J. Org. Chem.  1999,  64:  2186 
  CrossrefSearch in Google Scholar
• 4i Pénicaud V. Maillet C. Janvier P. Pipelier M. Bujoli B. Eur. J. Org. Chem.  1999,  1745 
  Crossref
• 4j Li X. Schenkel LB. Kozlowski MC. Org. Lett.  2000,  2:  875 
  CrossrefSearch in Google Scholar
• 4k Wiberg KB. Bailey WF. Tetrahedron Lett.  2000,  41:  9365 
  CrossrefSearch in Google Scholar
• 4l Barett S. O’Brien P. Steffens HC. Towers TD. Voith M. Tetrahedron  2000,  56:  9633 
  CrossrefSearch in Google Scholar
• For examples of 12-diamines as building blocks in ligand construction see:
• 5a Gao J.-X. Ikariya T. Noyori R. Organometallics  1996,  15:  1087 
  CrossrefSearch in Google Scholar
• 5b Trost BM. Shi Z. J. Am. Chem. Soc.  1996,  118:  3037 
  CrossrefSearch in Google Scholar
• 5c Trost BM. Bunt RC. Angew. Chem., Int. Ed. Engl.  1996,  35:  99 ; Angew. Chem. 1996, 108, 70
  CrossrefSearch in Google Scholar
• For examples see:
• 6a Kawashima M. Hirata R. Bull. Chem. Soc. Jpn.  1993,  66:  2002 
  Search in Google Scholar
• 6b Brunner H. Schiessling H. Angew. Chem., Int. Ed. Engl.  1994,  33:  125 ; Angew. Chem. 1994, 106, 130
  Search in Google Scholar
• 6c Alexakis A. Mangeney P. Marek I. Rose-Munch F. Rose R. Semra A. Robert F. J. Am. Chem. Soc.  1992,  114:  8288 
  Search in Google Scholar
• 6d Alexakis A. Mangeney P. Lensen N. Tranchier J.-P. Gosmini R. Raussou S. Pure Appl. Chem.  1996,  68:  531 
  Search in Google Scholar
• For examples see:
• 7a Kido J. Okamoto Y. Brittain HG. J. Org. Chem.  1991,  56:  1412 
  CrossrefSearch in Google Scholar
• 7b Alexakis A. Frutos JC. Mutti S. Mangeney P. J. Org. Chem.  1994,  59:  3326 
  CrossrefSearch in Google Scholar
• 7c Devitt PG. Mitchell MC. Weetman JM. Taylor RJ. Kee TP. Tetrahedron: Asymmetry  1995,  6:  2039 
  CrossrefSearch in Google Scholar
• 7d Staubach B. Buddrus J. Angew. Chem., Int. Ed. Engl.  1996,  35:  1344 ; Angew. Chem. 1996, 108, 1443
  CrossrefSearch in Google Scholar
• 8a Lippard SJ. Pure Appl. Chem.  1987,  59:  731 
  Search in Google Scholar
• 8b Pasini A. Zunino F. Angew. Chem., Int. Ed. Engl.  1987,  26:  615 ; Angew. Chem. 1987, 99, 632
  Search in Google Scholar
• 8c Reedijk J. Pure Appl. Chem.  1987,  59:  181 
  Search in Google Scholar
• 8d Hanessian S. Wang J. Can. J. Chem.  1993,  71:  886 
  Search in Google Scholar
• 9a Erickson JW. In Perspectives in Drug Discovery and Design   1993.  1:  p.109 
  CrossrefSearch in Google Scholar
• 9b De Clerq EJ. J. Med. Chem.  1995,  38:  2491 
  CrossrefSearch in Google Scholar
• 9c Hultén J. Bonham NM. Nillroth U. Hansson T. Zuccarello G. Bouzide A. Åqvist J. Classon B. Danielson UH. Karlén A. Kvarnström I. Samuelsson B. Hallberg A. J. Med. Chem.  1997,  40:  885 
  CrossrefSearch in Google Scholar
• For recent examples see:
• 10a Tanaka K. Sawanishi H. Tetrahedron: Asymmetry  2000,  11:  3837 
  CrossrefSearch in Google Scholar
• 10b Spielvogel D. Kammerer J. Keller M. Prinzbach H. Tetrahedron Lett.  2000,  41:  7863 
  CrossrefSearch in Google Scholar
• 10c Benedetti F. Norbedo S. Chem. Commun.  2001,  203 
  Crossref
• Diastereoselective synthesis of racemates:
• 11a Wei H.-X. Kim SH. Li G. J. Org. Chem.  2002,  67:  4777 
  CrossrefSearch in Google Scholar
• 11b Gómez Aranda V. Barluenga J. Aznar F. Synthesis 1974,  504 
  Crossref
• 11c Bäckvall J.-E. Tetrahedron Lett.  1975, 2225
  Crossref
• 11d Chong AO. Oshima K. Sharpless KB. J. Am. Chem. Soc.  1977,  99:  3420 
  CrossrefSearch in Google Scholar
• 11e Schofield MH. Kee TP. Anhaus JT. Schrock RR. Johnson KH. Davis WM. Inorg. Chem.  1991,  30:  3595 
  CrossrefSearch in Google Scholar
• 11f Jeong JU. Tao B. Sagasser I. Henniges H. Sharpless KB. J. Am. Chem. Soc.  1998,  120:  6844 
  CrossrefSearch in Google Scholar
• For recent examples see:
• 12a Laschat S. Fröhlich R. Wibbeling B. J. Org. Chem.  1996,  61:  2829 
  CrossrefSearch in Google Scholar
• 12b Laschat S. Liebigs Ann. Recl.  1997,  1 
  Crossref
• 12c Reetz MT. Schmitz A. Tetrahedron Lett.  1999,  40:  2741 ; and ref. cited therein
  CrossrefSearch in Google Scholar
• 12d Merino P. Lanaspa A. Merchan FL. Tejero T. Tetrahedron: Asymmetry  1998,  9:  629 
  CrossrefSearch in Google Scholar
• 12e Enders D. Chelain E. Raabe G. Bull. Soc. Chem. Fr.  1997,  134:  299 
  CrossrefSearch in Google Scholar
• 12f For a recent example of the synthesis of 13-diamines following this route see: Guerra FM. Mish MR. Carreira EM. Org. Lett.  2000,  2:  4265 
  CrossrefSearch in Google Scholar
• For recent examples see:
• 13a Shimizu M. Kamei M. Fujisawa T. Tetrahedron Lett.  1995,  36:  8607 
  CrossrefSearch in Google Scholar
• 13b Corey EJ. Lee D.-H. Sarshan S. Tetrahedron: Asymmetry  1995,  6:  3 
  CrossrefSearch in Google Scholar
• 13c Busacca CA. Campbell S. Dong Y. Grossbach D. Ridges M. Smith L. Spinelli E. J. Org. Chem.  2000,  65:  4753 
  CrossrefSearch in Google Scholar
• 13d Dell’Erba C. Novi M. Petrillo G. Spinelli D. Tavani C. Tetrahedron  1996,  52:  3313 
  CrossrefSearch in Google Scholar
• 14a Neumann WL. Rogic MM. Dunn TJ. Tetrahedron Lett.  1991,  32:  5865 
  CrossrefSearch in Google Scholar
• 14b Bambridge K. Begley MJ. Simpkins NS. Tetrahedron Lett.  1994,  35:  3391 
  CrossrefSearch in Google Scholar
• 14c Alvaro G. Grepioni F. Savoia D. J. Org. Chem.  1997,  62:  4180 
  CrossrefSearch in Google Scholar
• 14d Roland S. Mangeney P. Alexakis A. Synthesis  1999,  228 
  Crossref
• 14e Roland S. Mangeney P. Eur. J. Org. Chem.  2000,  611 
  Crossref
• 14f Alexakis A. Tomassini A. Chouillet C. Roland S. Mangeney R. Bernardinelli G. Angew. Chem. Int. Ed.   2000,  39:  4093 ; Angew. Chem. 2000, 112, 4259
  CrossrefSearch in Google Scholar
• 14g Martelli G. Morri S. Savoia D. Tetrahedron  2000,  56:  8367 
  CrossrefSearch in Google Scholar
• 14h Dondoni A. Perrone Rinaldi M. J. Org. Chem.  1998,  63:  9252 
  CrossrefSearch in Google Scholar
• 14i Enders D. Meiers M. Angew. Chem., Int. Ed. Engl.  1996,  35:  2261 ; Angew. Chem. 1996, 108, 2391
  CrossrefSearch in Google Scholar
• For examples see:
• 15a Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem Rev.  1994,  94:  2483 
  Search in Google Scholar
• 15b Richardson PF. Nelson LTJ. Sharpless KB. Tetrahedron Lett.  1995,  35:  9241 
  Search in Google Scholar
• 15c Skarzewski J. Gupta A. Tetrahedron: Asymmetry  1997,  8:  1861 
  Search in Google Scholar
• 15d Lee S.-G. Lee SH. Song C. Chung BY. Tetrahedron: Asymmetry  1999,  10:  1795 
  Search in Google Scholar
• 15e Lim C.-C. Mok KF. Sim KY. Leung P.-H. Tetrahedron: Asymmetry  1997,  8:  2045 
  Search in Google Scholar
• 15f Lee S.-G. Lim CW. Lee JK. Jung O.-S. Lee Y.-A. Tetrahedron: Asymmetry  2000,  11:  4709 
  Search in Google Scholar
• 15g Burgess K. Ibarzo J. Linthicum DS. Russell DH. Shin H. Shitangkoon A. Totani R. Zhang AJ. J. Am. Chem. Soc.  1997,  119:  1556 
  Search in Google Scholar
• 15h Lee S.-H. Yoon J. Nakamura K. Lee Y.-S. Org. Lett.  2000,  2:  1243 
  Search in Google Scholar
• 15i De Sousa SE. O’Brien P. Poumelle P. J. Chem. Soc., Perkin Trans 1  1998,  1483 
• 15j Liu Q. Marchington AP. Boden N. Rayner CM. J. Chem. Soc., Perkin Trans 1  1997,  511 
• 15k Osowska-Pacewicka K. Zwierzak A. Synthesis  1990,  505 
• 15l Orlek BS. Stemp G. Tetrahedron Lett.  1991,  32:  4045 
  Search in Google Scholar
• 15m Stingl K. Martens J. Liebigs Ann. Chem.  1994,  243 
• 15n Valasinas A. Frydman B. Friedmann HC. J. Org Chem.  1992,  57:  2158 
  Search in Google Scholar
• 16a Leung W.-H. Yu M.-T. Wu M.-C. Yeung L.-L. Tetrahedron Lett.  1996,  37:  891 
  CrossrefSearch in Google Scholar
• 16b Kuroki T. Katsuki T. Chem. Lett.  1995,  337 
  Crossref
• 16c Fuji K. Kawabata T. Kiryu Y. Sugiura Y. Heterocycles  1996,  42:  701 
  CrossrefSearch in Google Scholar
• 16d Maligres PE. See MM. Askin D. Reider PJ. Tetrahedron Lett.  1997,  38:  5253 
  CrossrefSearch in Google Scholar
• 16e Chandrasekhar M. Sekar G. Singh VK. Tetrahedron Lett.  2000,  41:  10079 
  CrossrefSearch in Google Scholar
• 16f Lee K.-D. Suh J.-M. Park J.-H. Ha J.-H. Choi HG. Park CS. Chang JW. Lee WK. Dong Y. Yun H. Tetrahedron  2001,  57:  8267 
  CrossrefSearch in Google Scholar
• For examples see:
• 17a Taniguchi N. Uemura M. Synlett  1997,  51 
  Crossref
• 17b Baruah B. Prajapati D. Sandhu JS. Tetrahedron Lett.  1995,  36:  6747 
  CrossrefSearch in Google Scholar
• 17c Shimizu M. Iida T. Fujisawa T. Chem. Lett.  1995,  609 
  Crossref
• 17d Kalyanam N. Venkateswara Rao G. Tetrahedron Lett.  1993,  34:  1647 
  CrossrefSearch in Google Scholar
• 17e Kammermeier B. Beck G. Jacobi D. Jendralla H. Angew. Chem., Int. Ed. Engl.  1994,  33:  685 ; Angew. Chem. 1994, 106, 719
  CrossrefSearch in Google Scholar
• 17f Yanada R. Negoro N. Okaniwa M. Miwa Y. Taga T. Yanada K. Fujita T. Synlett  1999,  5:  537 
  CrossrefSearch in Google Scholar
• 17g Campos PJ. Arranz J. Rodríguez MA. Tetrahedron  2000,  56:  7285 
  CrossrefSearch in Google Scholar
• 17h Shimizu M. Niwa Y. Tetrahedron Lett.  2001,  42:  2829 
  CrossrefSearch in Google Scholar
• 18a Enders D. Wiedemann J. Synthesis  1996,  1443 
  Crossref
• 18b Lucet D. Toupet L. Le Gall T. Mioskowski C. J. Org. Chem.  1997,  62:  2682 
  CrossrefSearch in Google Scholar
• 18c Imagawa K. Hata E. Yamada T. Mukaiyama T. Chem. Lett.  1996,  291 
  Crossref
• 18d Leroux M.-L. Le Gall T. Mioskowski C. Tetrahedron: Asymmetry  2001,  12:  1817 ; and references cited therein
  CrossrefSearch in Google Scholar
• 19a Seo R. Ishizuka T. Abdel-Aziz AA.-M. Kunieda T. Tetrahedron Lett.  2001,  42:  6353 
  CrossrefSearch in Google Scholar
• 19b Sprott KT. McReynolds MD. Hanson PR. Org. Lett.  2001,  3:  3939 
  CrossrefSearch in Google Scholar
• 20 Adams H. Anderson JC. Peace S. Pennell AMK. J. Org. Chem.  1998,  63:  9932 
  CrossrefSearch in Google Scholar
• 21 Yamauchi T. Higashiyama K. Kubo H. Ohmiya S. Tetrahedron: Asymmetry  2000,  11:  3003 
  CrossrefSearch in Google Scholar
• 22a Enders D. Schiffers R. Synthesis  1996,  53 
• 22b Coldham I. Copley RCB. Haxell TFN. Howard S. Org. Lett.  2000,  3:  3799 
  Search in Google Scholar
• 23 Kaiser A. Balbi M. Tetrahedron: Asymmetry  1999,  10:  1001 
  CrossrefSearch in Google Scholar
• For recent reviews on the 12-addition of organometallic reagents to the CN double bond see:
• 24a Denmark SE. Nicaise OJ.-C. Chem. Commun.  1996,  999 
  Thieme Connect
• 24b Enders D. Reinhold U. Tetrahedron: Asymmetry  1997,  8:  1895 
  Thieme ConnectSearch in Google Scholar
• 24c Bloch R. Chem. Rev.  1998,  98:  1407 
  Thieme ConnectSearch in Google Scholar
• 24d Kobayashi S. Ishitani H. Chem. Rev.  1999,  99:  1069 
  Thieme ConnectSearch in Google Scholar
• 24e Merino P. Franco S. Merchan FL. Tejero T. Synlett  2000,  442 
  Thieme Connect
• 24f Alvaro G. Savoia D. Synlett  2002,  651 
  Thieme Connect
• For reviews on the SAMP/RAMP hydrazone method see:
• 25a Enders D. In Asymmetric Synthesis   Vol. 3B:  Morrison JD. Academic Press; Orlando: 1984.  p.275 
  CrossrefSearch in Google Scholar
• 25b Enders D. Fey P. Kipphardt H. Org. Synth.  1987,  65:  173-183  
  CrossrefSearch in Google Scholar
• 25c Enders D. Klatt M. In Encyclopedia of Reagents for Organic Synthesis   Paquette LA. Wiley; New York: 1995.  p.178 
  Crossref
• 25d Job A. Janeck CF. Bettray W. Peters R. Enders D. Tetrahedron  2002,  58:  2253 
  CrossrefSearch in Google Scholar
• 26a Imamoto T. Takiyama N. Nakamura K. Tetrahedron Lett.  1985,  26:  4763 
  CrossrefSearch in Google Scholar
• 26b Imamoto T. Sugiura Y. J. Organomet. Chem.  1985,  285:  C21 
  CrossrefSearch in Google Scholar
• 26c Imamoto T. Sugiura Y. Takiyama N. Tetrahedron Lett.  1984,  25:  4233 
  CrossrefSearch in Google Scholar
• 26d Imamoto T. Kusumoto T. Tawarayama Y. Sugiura Y. Mita T. Hatanaka Y. Yokoyama M. J. Org. Chem.  1984,  49:  3904 
  CrossrefSearch in Google Scholar
• 27a Nübling C. Dissertation   RWTH Aachen; Germany: 1987. 
  Thieme Connect
• 27b Denmark SE. Nicaise O. Edwards JP. J. Org. Chem.  1990,  55: 6219 For recent examples see:
  Thieme ConnectSearch in Google Scholar
• 27c Enders D. Teschner P. Gröbner R. Raabe G. Synthesis  1999,  247 
  Thieme Connect
• 27d Enders D. Teschner P. Raabe G. Heterocycles  2000,  52:  733 
  Thieme ConnectSearch in Google Scholar
• 27e Enders D. Kallfass U. Nolte B. Synlett  2002,  33 
  Thieme Connect
• 28a Enders D. Funk R. Klatt M. Raabe G. Hovestreydt ER. Angew. Chem., Int. Ed. Engl.  1993,  32:  418 ; Angew. Chem. 1993, 105, 418
  Thieme ConnectSearch in Google Scholar
• 28b Enders D. Klatt M. Funk R. Synlett  1993,  226 
  Thieme Connect
• 28c Lochtman R. Dissertation   RWTH Aachen; Germany: 1997. 
  Thieme Connect
• 29a Feuer H. Brown F. J. Org. Chem.  1970,  35:  1468 
  CrossrefSearch in Google Scholar
• 29b Yamazaki N. Suzuki H. Aoyagi S. Kibayashi C. Tetrahedron Lett.  1996,  37:  6161 
  CrossrefSearch in Google Scholar
• 30a Enders D. Lochtman R. Synlett  1997,  355 
• 30b Meiers M. Dissertation   RWTH Aachen; Germany: 1997. 
• 30c Enders D. Lochtmann R. Meiers M. Müller S. Lazny R. Synlett  1998,  1182  For recent examples of the BH₃ ·THF cleavage of hydrazines applied in natural product synthesis see:
• 30d Enders D. Thiebes C. Synlett  2000,  1745 
• 30e Enders D. Kirchhoff JH. Synthesis  2000,  2099 
• 30f Enders D. Nolte B. Raabe G. Runsink J. Tetrahedron: Asymmetry  2002,  13:  285 
  Search in Google Scholar
• 31 Tietze LF. Eicher T. In Reaktionen und Synthesen im Organisch-Chemischen Praktikum und Forschungslaboratorium   2nd Ed.:  Georg Thieme Verlag; Stuttgart: 1991. 
  Search in Google Scholar
• 32 Enders D. Eichenauer H. Chem. Ber.  1979,  122:  2933 
  Search in Google Scholar
• 33 Ehlers J. tom Dieck H. Z. Anorg. Allg. Chem.  1980,  560:  80 
  Search in Google Scholar
• 34 Nantz MH. Lee DA. Bender DM. Roohi AH. J. Org. Chem.  1992,  57:  6653 
  CrossrefSearch in Google Scholar
• 35 Kise N. Oike H. Okazaki E. Masami Y. Shono T. J. Org. Chem.  1995,  60:  3980 
  Search in Google Scholar