Rh/手性磷酸协同催化羰基酰和(Z)-3-苄基- 3h -吲哚的立体选择性(3 + 3)-环环反应

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-28 Epub Date: 2025-02-19 DOI:10.1021/acs.orglett.5c00188

Jyotish Barman, Spoorthi Ananda, Subhas Chandra Pan

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引用次数: 0

摘要

报道了一种非映对和对映选择性（3 + 3）环环原位生成的羰基酰和(Z)-3-苄基- 3h -吲哚通过Rh/手性磷酸协同催化实现。这项研究首次描述了环七[b]吲哚的对映选择性合成与氧-桥接基序。反应范围广，氧桥接环七[b]吲哚产物收率中至高，具有优异的非对映选择性和良好至高的对映选择性。

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Stereoselective (3 + 3)-Cycloannulation of Carbonyl Ylides and (Z)-3-Benzylidene-3H-indoles Enabled by Cooperative Rh/Chiral Phosphoric Acid Catalysis.

A diastereo- and enantioselective (3 + 3)-cycloannulation of in situ generated carbonyl ylides and (Z)-3-benzylidene-3H-indoles enabled by cooperative Rh/chiral phosphoric acid catalysis is reported. This study is the first to describe an enantioselective synthesis of cyclohepta[b]indole with an oxa-bridged motif. The scope of the reaction is broad, and the oxa-bridged cyclohepta[b]indole products were obtained in moderate to good yields and with excellent diastereoselectivities and good to high enantioselectivities.

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来源期刊

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.