Origin of the diastereoselection in the indium-mediated addition of haloallylic sulfones to aldehydes

被引：15

作者：

Min, JH

Jung, SY

Wu, B

Oh, JT

Lah, MS

Koo, S ^{[1
]}

机构：

[1] Myong Ji Univ, Dept Chem, Yongin 449728, Kyunggi, South Korea

[2] Hanyang Univ, Coll Sci, Dept Chem, Ansan 425791, Kyunggi, South Korea

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 07期

关键词：

D O I：

10.1021/ol060297r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The R-1 substituents at C(2) of the haloallylic sulfones 1 play a pivotal role in controlling the diastereoselectivity of the indium-mediated addition reaction to benzalclehyde to produce the homoallylic alcohols 3. The R, Me group of 1 prefers the chair form in the In-coordinated six-membered cyclic transition state to give anti-3a, and the R-1 Ph group of 1 favors the twist boat form to give syn-3n, both in a high 13:1 selectivity.

引用

页码：1459 / 1462

页数：4

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