Remote Asymmetric Induction with Vinylketene SilylN,O-Acetal
Journal of the American Chemical Society2004Vol. 126(42), pp. 13604–13605
Citations Over TimeTop 10% of 2004 papers
Shin-ichi Shirokawa, Masato Kamiyama, Tomoaki Nakamura, Masakazu Okada, Atsuo Nakazaki, Seijiro Hosokawa, Susumu Kobayashi
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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