Enantioselective De Novo Synthesis of α,α‐Diaryl Ketones from Alkynes

Author:

Zhou Xueting12ORCID,Huang Qingqin12,Guo Jiami12,Dai Lei2ORCID,Lu Yixin12ORCID

Affiliation:

1. Joint School of National University of Singapore Tianjin University International Campus of Tianjin University Binhai New City Fuzhou 350207 China

2. Department of Chemistry National University of Singapore 3 Science Drive 3 117543 Singapore Singapore

Abstract

AbstractChiral α,α‐diaryl ketones are structural motifs commonly present in bioactive molecules, and they are also valuable building blocks in synthetic organic chemistry. However, catalytic asymmetric synthesis of α,α‐diaryl ketones bearing a tertiary stereogenic center remains largely unsolved. Herein, we report a catalytic de novo enantioselective synthesis of α,α‐diaryl ketones from simple alkynes via chiral phosphoric acid (CPA) catalysis. A broad range of enolizable α,α‐diaryl ketones are prepared in good yields and with excellent enantioselectivities. The described protocol also serves as an efficient deuteration method for the preparation of enantiomerically enriched deuterated α,α‐diaryl ketones. Using the methodology reported, bioactive molecules, including one of the best‐selling anti‐breast cancer drugs, tamoxifen, are readily synthesized.

Funder

National Research Foundation Singapore

Publisher

Wiley

Subject

General Chemistry,Catalysis

Reference62 articles.

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