α-卤代烯醛的立体选择性乙烯基型向山羟醛反应。

Stereoselective vinylogous Mukaiyama aldol reaction of α-haloenals.

作者信息

Iwasaki Yoichi, Matsui Ryosuke, Suzuki Takahiro, Nakazaki Atsuo, Kobayashi Susumu

机构信息

Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2011;59(4):522-4. doi: 10.1248/cpb.59.522.

DOI:10.1248/cpb.59.522

PMID:21467689

Abstract

We have developed a high-yielding and stereoselective vinylogous Mukaiyama aldol reaction (VMAR) of α-haloenals. Contrary to the simple α,β-unsaturated aldehyde, α-haloenals were found to be reactive affording the corresponding VMAR adducts in excellent yields. Some transformations of VMAR adducts by Pd-mediated cross-coupling were also examined in order to demonstrate the synthetic utility of VMAR of α-haloenals.

摘要

我们开发了一种高产率且具有立体选择性的α-卤代烯醛的乙烯基Mukaiyama羟醛缩合反应（VMAR）。与简单的α,β-不饱和醛不同，发现α-卤代烯醛具有反应活性，能以优异的产率得到相应的VMAR加合物。为了证明α-卤代烯醛的VMAR的合成效用，还研究了钯介导的交叉偶联对VMAR加合物的一些转化反应。