title: Remote asymmetric induction with vinylketene silyl n,o-acetal.
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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Nodashi, Chiba 278-8510, Japan.
authors.forename: Shin-Ichi
authors.initials: S
authors.lastname: Shirokawa
authors.forename: Masato
authors.initials: M
authors.lastname: Kamiyama
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Nakamura
authors.forename: Masakazu
authors.initials: M
authors.lastname: Okada
authors.forename: Atsuo
authors.initials: A
authors.lastname: Nakazaki
authors.forename: Seijiro
authors.initials: S
authors.lastname: Hosokawa
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi