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DOI: 10.1055/s-2008-1077999
Enantioselective Arylzinc Addition to Aldehydes
Contributor(s):Hisashi Yamamoto, Joshua N. PayetteUniversity of Virginia, Charlottesville, USA
Activation of Functional Arylzincs Prepared from Aryl Iodides and Highly Enantioselective Addition to Aldehydes
Org. Lett. 2008, 10: 2709-2712
Publication History
Publication Date:
22 August 2008 (online)
Key words
zinc - aldehyde addition - arylzinc
Significance
In the present work, the authors utilize Knochel’s method for diarylzinc preparation (Angew. Chem. Int. Ed. 2004, 43, 1017) and (S)-H8BINOL-derived L1 to generate a highly reactive and enantioselective catalytic system for the addition of various functionalized arylzincs to aldehydes. Interestingly, when L1 was not added the reaction rate was significantly decreased.
Comment
In situ preparation of arylzinc reagents with subsequent enantioselective addition to aldehydes have been reported where arylzinc species are generated involving combinations of arylboronic acids and Et2Zn or aryl bromides, n-BuLi, and ZnCl2 (C. Bolm, J. Rudolph J. Am. Chem. Soc. 2002, 124, 14850; J. G. Kim, P. J. Walsh Angew. Chem. Int. Ed. 2006, 45, 4175). This paper demonstrates the utility of Knochel’s method and provides an alternative approach to generate chiral carbinols via arylzinc addition reactions.