Highly enantioselective mukaiyama aldol reactions catalyzed by a chiral oxazaborolidinium ion: total synthesis of (-)-inthomycin C.

Department of Chemistry, Sungkyunkwan University, Suwon, 440-746, Korea.
Organic Letters (Impact Factor: 6.14). 10/2010; 12(22):5088-91. DOI: 10.1021/ol102234k
Source: PubMed

ABSTRACT A cationic oxazaborolidinium-catalyzed asymmetric Mukaiyama aldol reaction of (1-methoxy-2-methyl-propenyloxy)-trimethylsilane with various aldehydes including α,β-disubstituted acroleins has been developed in high yields and enantioselectivities. The synthetic utility of this methodology was demonstrated in the first short synthesis of naturally occurring inthomycin C in high enantiopurity.

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