2-氨基-3取代吲哚的有机催化立体发散脱芳化和n -酰化

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Lunfeng Chen, Pengfei Li
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引用次数: 0

摘要

首次实现了2-氨基-3取代吲哚的有机催化化学和对映选择性反应。通过森田-贝里斯-希尔曼碳酸酯的不对称烯丙基烷基化反应,2-氨基-3-取代吲哚的有机催化对映选择性脱芳化反应得到了一系列具有季碳立体中心的3,3-二取代吲哚-2-亚胺,产率为34-79%,ee为61-91%。以Boc2O为反应伙伴,建立了2-氨基-3取代吲哚的有机催化对映选择性n -酰化反应,产率为22-98%,ee为73-92%。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles

Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles
Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, organocatalytic enantioselective dearomatization of 2-amino-3-subsituted indoles afforded an array of enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34–79% yields with 61–91% ee. With Boc2O as reaction partner, the organocatalytic enantioselective N-acylation of 2-amino-3-subsituted indoles was established to furnish C-N axially chiral products in 22–98% yields with 73–92% ee.
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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