Abstract
The scope of the asymmetric silyl transfer to unsaturated lactones utilising a C2-symmetric NHC-Cu(I) catalyst has been established and kinetic resolutions mediated by silyl transfer have been used to prepare enantiomerically enriched anti-4,5-disubstituted 5-membered lactones. The method has been exploited in an expedient synthesis of (+)-blastmycinone.
Highlights
The scope of the asymmetric silyl transfer to unsaturated lactones utilising a C2-symmetric N-heterocyclic carbene (NHC)–Cu(I) catalyst has been established and kinetic resolutions mediated by silyl transfer have been used to prepare enantiomerically enriched anti-4,5-disubstituted 5-membered lactones
The method has been exploited in an expedient synthesis of (+)-blastmycinone
The b-hydroxy carbonyl moiety is synonymous with the aldol reaction and is a well-known motif: the ability to efficiently generate this valuable motif in stereoselective fashion remains an important goal in modern synthetic chemistry
Summary
NHC–Cu(I) catalysed asymmetric conjugate silyl transfer to unsaturated lactones: application in kinetic resolution† The scope of the asymmetric silyl transfer to unsaturated lactones utilising a C2-symmetric NHC–Cu(I) catalyst has been established and kinetic resolutions mediated by silyl transfer have been used to prepare enantiomerically enriched anti-4,5-disubstituted 5-membered lactones. Lactone substrates, have been described.[6,8] in general, asymmetric conjugate additions to 5-membered substrates are known to be challenging.[10] In this Communication we describe our studies to optimise and establish the scope of the Cu-catalysed asymmetric silyl transfer to unsaturated lactones.
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