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Enantioselective Construction of Tertiary C(sp3)−P Bonds by Thiourea‐based Bifunctional Phosphonium Salt‐catalyzed Hydrophosphonylation of Ketone Compounds
Author(s) -
Feng Zhenghuai,
Zhang Hongkui,
Ren Xiaoyu,
Jiang Chunhui,
Gao Guowei,
Wang Tianli
Publication year - 2021
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202100799
Subject(s) - bifunctional , enantioselective synthesis , chemistry , phosphonate , thiourea , phosphonium , ketone , catalysis , salt (chemistry) , organic chemistry , phosphonium salt , hydrogen bond , combinatorial chemistry , molecule
Asymmetric hydrophosphonylation of carbonyl compounds to generate a variety of optically pure quaternary α ‐hydroxy phosphonate molecules is herein described by thiourea‐derived bifunctional phosphonium salt catalysis. This new synthetic protocol has an excellent functional group tolerance, and particularly both aromatic, heteroaromatic and aliphatic α ‐ketoesters and 1,2‐diketones were readily transferred into phosphonate products in high yields (up to 99 %) with excellent enantioselectivities (up to 97 % ee). The mechanistic results suggested that both ion pair and hydrogen‐bonding interactions were crucial in asymmetric induction.