doi: 10.1021/ja0465855.
Remote asymmetric induction with vinylketene silyl n,o-acetal
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- PMID: 15493903
- DOI: 10.1021/ja0465855
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Remote asymmetric induction with vinylketene silyl n,o-acetal
J Am Chem Soc.
.
Abstract
A highly regio- and diastereoselective TiCl4-mediated vinylogous Mukaiyama aldol reaction using the chiral vinylketene silyl N,O-acetal has been developed. The present vinylogous Mukaiyama aldol reaction provides a unique and effective means of controlling remote asymmetric induction. The methyl group at the alpha-position is important in achieving a high level of stereoselectivity. From a synthetic point of view, this methodology can provide a one-step construction of delta-hydroxy-alpha,gamma-dimethyl-alpha,beta-unsaturated carbonyl unit that is seen in many natural polyketide products.
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