Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers
Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers
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DOI：
10.1021/ol016738i
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发表时间：
2001-11-15
期刊：
影响因子：
5.2
通讯作者：
Musselman, RA
中科院分区：
文献类型：
--
作者：
Boeckman, RK;Boehmler, DJ;Musselman, RA
[图表]一种新的衍生内酰胺助剂的烯醇化物显示出非常高的非对映选择性单烷基化。与反应性烷基化剂发生第二次烷基化，得到季中心也具有高的非对映选择性。与所提出的非对映选择性模型雅阁，烯醇化锂和烯醇化钠提供具有相反意义的不对称诱导的产物。
[GRAPHICS]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.