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手性锂酰胺作为无痕迹助剂的高对映选择性芳基乙酸直接烷基化反应。

Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries.

机构信息

Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.

出版信息

J Am Chem Soc. 2011 Aug 10;133(31):11936-9. doi: 10.1021/ja205107x. Epub 2011 Jul 15.

DOI:10.1021/ja205107x
PMID:21744818
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3373785/
Abstract

A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.

摘要

一种直接、高对映选择性的通过烯醇化物对芳基乙酸进行烷基化的方法已经被开发出来,该方法使用易得的手性氨基锂作为立体导向试剂。这种方法避免了目前用于这种类型转化的传统手性辅助剂的连接和去除。该方案操作简单,手性试剂易于回收。

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2
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Org Lett. 2011 May 20;13(10):2734-7. doi: 10.1021/ol200834p. Epub 2011 Apr 21.
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Chemistry. 2023 Jan 18;29(4):e202202575. doi: 10.1002/chem.202202575. Epub 2022 Dec 8.
5
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7
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