Origin of the diastereoselection in the indium-mediated addition of haloallylic sulfones to aldehydes.
作者信息
Min Jae-Hong, Jung Se-Young, Wu Bo, Oh Jung Taek, Lah Myoung Soo, Koo Sangho
机构信息
Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea.
出版信息
Org Lett. 2006 Mar 30;8(7):1459-62. doi: 10.1021/ol060297r.
PMID:16562916
Abstract
[reaction: see text] 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 benzaldehyde to produce the homoallylic alcohols 3. The R(1) 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.
摘要
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