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Efficient Access to Chiral β‐Borylated Carboxylic Esters via Rh‐Catalyzed Hydrogenation
Author(s) -
Liu Gang,
Li Anqi,
Qin Xueyuan,
Han Zhengyu,
Dong XiuQin,
Zhang Xumu
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900161
Subject(s) - chemistry , yield (engineering) , catalysis , furan , thiourea , asymmetric hydrogenation , ligand (biochemistry) , medicinal chemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , receptor , biochemistry , materials science , metallurgy
Abstract Rh/bisphosphine−thiourea ligand (ZhaoPhos)‐catalyzed asymmetric hydrogenation of ( Z )‐β‐substituted‐β‐boryl‐α,β‐unsaturated esters was successfully developed, furnishing a variety of chiral β‐borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram‐scale asymmetric hydrogenation was performed efficiently in the presence of only 0.05 mol% (S/C=2 000) catalyst loading with full conversion, 99% yield and 99% ee. Moreover, the hydrogenation product was easily converted to other versatile synthetic intermediates, such as methyl ( S )‐3‐hydroxy‐3‐phenylpropanoate and methyl ( S )‐3‐(furan‐2‐yl)‐3‐phenylpropanoate.