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Catalytic Asymmetric 1,4-Type Friedel-Crafts (Hetero)Arylation of 1-Azadienes: Highly Enantioselective Synthesis of Chiral Hetero-Triarylmethanes

Abstract

The direct enantioselective Michael-type Friedel-Crafts arylation and heteroarylation of s-cis 1-azadienes were achieved by the catalysts of chiral bifunctional tertiary amine-ureas for 2-naphthols as nucleophiles, and phosphoric acids for indoles as nucleophiles. These two catalytic protocols efficiently enabled access to diverse important benzofuran-containing hetero-triaylmethanes in up to 98% yield and 99.5:0.5 e.r.

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Article information


Submitted
20 Nov 2019
Accepted
03 Jan 2020
First published
06 Jan 2020

Org. Chem. Front., 2020, Accepted Manuscript
Article type
Research Article

Catalytic Asymmetric 1,4-Type Friedel-Crafts (Hetero)Arylation of 1-Azadienes: Highly Enantioselective Synthesis of Chiral Hetero-Triarylmethanes

C. Wang, Q. Yang, M. Wang, Y. Shang, X. Tong, Y. Deng and Z. shao, Org. Chem. Front., 2020, Accepted Manuscript , DOI: 10.1039/C9QO01391A

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