Synthesis 2018; 50(23): 4577-4590
DOI: 10.1055/s-0037-1610250
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© Georg Thieme Verlag Stuttgart · New York

Chiral Pyrophosphoric Acid Catalysts for the para-Selective and Enantioselective Aza-Friedel–Crafts Reaction of Phenols

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This work was financially supported by JSPS KAKENHI Grant Numbers JP26288046, JP17H03054, and JP15H05810 in Precisely Designed Catalysts with Customized Scaffolding.
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Publication History

Received: 27 June 2018

Accepted after revision: 24 July 2018

Publication Date:
22 August 2018 (online)


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Abstract

Chiral BINOL-derived pyrophosphoric acid catalysts were developed and used for the regio- and enantioselective aza-Friedel–Crafts reaction of phenols with aldimines. ortho/para-Directing phenols could react at the para-position selectively with moderate to good enantioselectivities. Moreover, the gram-scale transformation of a product into the key intermediate for the antifungal agent (R)-bifonazole was demonstrated.

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