前手性3,4-熔融吡咯有机催化不对称Friedel-Crafts反应的去对称/动力学解析序列。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-17 DOI:10.1021/acs.orglett.5c03731

Rupkumar Khuntia,Sujan Sarkar,Ankita Roy,Subhas Chandra Pan

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引用次数: 0

摘要

一个有趣但未被充分探索的话题是源自不对称取代的杂芳烃环的杂芳烃衍生物的中心手性。在此，我们首次证明了前手性3,4-熔融吡咯的催化对映选择性Friedel-Crafts反应。烯丙酰胺作为亲电试剂，一种容易获得的磷酸作为催化剂。通过脱对称和动力学分解两个不对称过程，先后制备了具有高对映选择性（高达98:2）的2-取代3,4-熔融多环吡咯。并将产物精制成具有合成挑战性的手性异吲哚化合物。

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Organocatalytic Asymmetric Friedel-Crafts Reaction of Prochiral 3,4-Fused Pyrroles via a Desymmetrization/Kinetic Resolution Sequence.

An intriguing but underexplored topic is the central chirality in heteroarene derivatives originating from unsymmetrically substituted heteroarene rings. Herein, we demonstrate the first catalytic enantioselective Friedel-Crafts reaction of prochiral 3,4-fused pyrroles. Allenamides are used as the electrophiles, and an easily available phosphoric acid was employed as the catalyst. Desymmetrization and kinetic resolution, two asymmetric processes, were used successively to produce polycyclic 2-substituted, 3,4-fused pyrroles with high enantioselectivities (up to 98:2 er). Also, the products were elaborated into synthetically challenging chiral isoindole compounds.

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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.