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

Angew Chem Int Ed Engl. 2023 Sep 19:e202310078. doi: 10.1002/anie.202310078. Online ahead of print.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.PMID:37724448 | DOI:10.1002/anie.202310078

Source: Angewandte Chemie - September 19, 2023 Category: Chemistry Authors: Xueting Zhou Qingqin Huang Jiami Guo Lei Dai Yixin Lu Source Type: research