Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline) (DBFOX/Ph)

被引:61
作者
Iserloh, U
Curran, DP [1 ]
Kanemasa, S
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
[2] Kyushu Univ, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0957-4166(99)00238-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A high-yielding synthesis (50% overall yield) of tridentate bisoxazoline ligand (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) (DBFOX/Ph) was developed. DBFOX/Ph was subsequently tested in enantioselective conjugate radical additions onto 3-(3-phenyl-2-propenoyl)-2-oxazolidinone Two dozen Lewis acids were evaluated, and Mg(ClO4)(2) emerged as the best Lewis acid in terms of yield and enantioselectivity (100% yield, 75.4% ee (S)). (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2417 / 2428
页数:12
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