迈向通用手性助剂的开发。9. 形成叔碳和季碳中心的高非对映选择性烷基化和酰基化反应。
Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers.
作者信息
Boeckman R K, Boehmler D J, Musselman R A
机构信息
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA.
出版信息
Org Lett. 2001 Nov 15;3(23):3777-80. doi: 10.1021/ol016738i.
PMID:11700136
Abstract
[reaction--see text] Enolates of a new camphor-derived lactam auxiliary are shown to monoalkylate with very high diastereoselectivity. A second alkylation occurs with reactive alkylating agents to afford quaternary centers also with high diastereoselectivity. In accord with a proposed model for diastereoselection, lithium and sodium enolates provide products with an opposite sense of asymmetric induction.
摘要
[反应——见正文] 一种新的樟脑衍生内酰胺助剂的烯醇盐显示出以非常高的非对映选择性进行单烷基化反应。与活性烷基化剂发生的第二次烷基化反应也能以高非对映选择性得到季碳中心。与所提出的非对映选择性模型一致，锂烯醇盐和钠烯醇盐提供的产物具有相反的不对称诱导方向。
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