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Asymmetric Ring Opening of meso ‐Epoxides with Aromatic Amines Catalyzed by a New Proline‐Based N , N′ ‐Dioxide‐Indium Tris(triflate) Complex
Author(s) -
Gao Bo,
Wen Yuehong,
Yang Zhigang,
Huang Xiao,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2008
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.200700474
Subject(s) - chemistry , trifluoromethanesulfonate , catalysis , indium , tris , proline , ring (chemistry) , epoxide , combinatorial chemistry , organic chemistry , medicinal chemistry , polymer chemistry , amino acid , biochemistry
The catalytic asymmetric ring opening of meso ‐epoxides with aromatic amines was achieved using a new proline‐based N , N′ ‐dioxide‐indium tris(triflate) complex in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee ) under mild conditions. The coordination ability of N , N′ ‐dioxide 1c was investigated by X‐ray and NMR analysis. A plausible seven‐coordinate transition state model was proposed. The chiral N , N′ ‐dioxides surveyed were synthesized from proline through only three conventional steps. The procedure could be run on a gram‐scale without any loss of enantioselectivity. This protocol provides a highly practical and useful tool for the bulky preparation of optically pure β ‐amino alcohols.