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Enantioselective Copper(II)‐Catalyzed Conjugate Addition of Indoles to β ‐ Substituted Unsaturated Acyl Phosphonates
Author(s) -
Ma HongLi,
Xie Lei,
Zhang ZhenHua,
Li JiaQi,
Qin ZhaoHai,
Fu Bin
Publication year - 2016
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.201500923
Subject(s) - chemistry , enantioselective synthesis , oxazoline , conjugate , catalysis , adduct , indole test , alkyl , copper , ligand (biochemistry) , organic chemistry , aryl , medicinal chemistry , combinatorial chemistry , receptor , mathematical analysis , biochemistry , mathematics
Abstract The first copper‐catalyzed enantioselective conjugate addition of indoles to β‐substituted unsaturated acyl phosphonates was successfully realized by using a heteroarylidene‐tethered bis(oxazoline) ligand. The reaction features high efficiency, cheap catalyst and broad generality. In the case of either β‐alkyl‐ or β‐aryl‐substituted unsaturated acyl phosphonates, the 3‐indolyl adducts were achieved in high yields with good to excellent enantioselectivities (up to 97% ee ). The 3‐indolyl adducts can serve as important intermediates in the synthesis of indole alkaloids.