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
收藏
页码：1459 / 1462
页数：4
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