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Catalytic asymmetric 1,4-type Friedel–Crafts (hetero)arylations of 1-azadienes: the highly enantioselective syntheses of chiral hetero-triarylmethanes

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Abstract

Direct enantioselective Michael-type Friedel–Crafts arylations and heteroarylations of s-cis 1-azadienes were achieved by applying chiral bifunctional tertiary amine-urea catalysts when using 2-naphthols as the nucleophiles, and phosphoric acid catalysts when using indoles as the nucleophiles. These two catalytic protocols efficiently enabled access to a diverse variety of important benzofuran-containing hetero-triarylmethanes in up to 98% yield and with 99.5 : 0.5 er.

Graphical abstract: Catalytic asymmetric 1,4-type Friedel–Crafts (hetero)arylations of 1-azadienes: the highly enantioselective syntheses of chiral hetero-triarylmethanes

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Article information


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

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Catalytic asymmetric 1,4-type Friedel–Crafts (hetero)arylations of 1-azadienes: the highly enantioselective syntheses of chiral hetero-triarylmethanes

C. Wang, Q. Yang, M. Wang, Y. Shang, X. Tong, Y. Deng and Z. Shao, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01391A

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