Remote asymmetric induction with viny ketene silyl N,O-acetal

被引：153

作者：

Shirokawa, SI ^{[1
]}

Kamiyama, M ^{[1
]}

Nakamura, T ^{[1
]}

Okada, M ^{[1
]}

Nakazaki, A ^{[1
]}

Hosokawa, S ^{[1
]}

Kobayashi, S ^{[1
]}

机构：

[1] Tokyo Univ Sci, RIKADAI, Fac Pharmaceut Sci, Chiba 2788510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 42期

关键词：

D O I：

10.1021/ja0465855

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 α-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 δ-hydroxy-α,γ-dimethyl-α,β-unsaturated carbonyl unit that is seen in many natural polyketide products. Copyright © 2004 American Chemical Society.

引用

页码：13604 / 13605

页数：2

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