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Synfacts 2009(4): 0407-0407
DOI: 10.1055/s-0028-1087906
DOI: 10.1055/s-0028-1087906
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New YorkLewis Acid Catalyzed C-H Bond Functionalization/Hydride Transfer
Contributor(s):Mark Lautens, Praew ThansandoteK. M. McQuaid, D. Sames*
Columbia University, New York, USA
C-H Bond Functionalization via Hydride Transfer: Lewis Acid Catalyzed Alkylation Reactions by Direct Intramolecular Coupling of sp³ C-H Bonds and Reactive Alkenyl Oxocarbenium Intermediates
J. Am. Chem. Soc. 2009, 131: 402-403
Columbia University, New York, USA
C-H Bond Functionalization via Hydride Transfer: Lewis Acid Catalyzed Alkylation Reactions by Direct Intramolecular Coupling of sp³ C-H Bonds and Reactive Alkenyl Oxocarbenium Intermediates
J. Am. Chem. Soc. 2009, 131: 402-403
Further Information
Publication History
Publication Date:
23 March 2009 (online)
Key words
Lewis acid catalysis - C-H functionalization - hydride transfer - sp³ C-H bond
Significance
The authors report a transition-metal free hydride transfer/cyclization reaction activated by Lewis acidic boron. A preliminary scope is reported with good yields and diastereoselectivities. Notably, a substrate derived from (-)-menthol provided a single diastereomer.
Comment
Overall, the reaction constitutes a formal C-H bond activation. Adding ethylene glycol to conjugated ketone substrates eliminated the use of preformed ketals. These in situ reactions were much faster and provided higher yields and diastereoselectivities compared to the use of the Lewis acid by itself.