Rhodium-Catalyzed Asymmetric Annulation of Unactivated Alkynes with 3‑(ortho-Boronated Aryl) Conjugated Enones: Enantioselective Synthesis of 2,3-Disubstituted Indenes

A rhodium-catalyzed tandem arylation/cyclization reaction of 3-(ortho-boronated aryl) conjugated enones with unactivated alkynes is reported. By using a rhodium­(I)/chiral-diene complex as the catalyst, the protocol was processed smoothly to provide various 2,3-disubstituted indene compounds in high...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-05, Vol.88 (9), p.6140-6145
Main Authors: Sun, Yu, Pan, Jiayu, Wang, Xiuqi, Bu, Xiaoli, Ma, Mengtao, Xue, Fei
Format: Article
Language:English
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Summary:A rhodium-catalyzed tandem arylation/cyclization reaction of 3-(ortho-boronated aryl) conjugated enones with unactivated alkynes is reported. By using a rhodium­(I)/chiral-diene complex as the catalyst, the protocol was processed smoothly to provide various 2,3-disubstituted indene compounds in high yields with excellent regioselectivities and enantioselectivities. The approach outlined herein is appealing, as simple diarylalkynes, diakylalkynes, and alkyl­(aryl)­alkynes are the starting materials.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02957