Bifunctional Catalyst Promotes Highly Enantioselective Bromolactonizations To Generate Stereogenic C-Br Bonds

被引:159
作者
Paull, Daniel H. [1 ]
Fang, Chao [1 ]
Donald, James R. [1 ]
Pansick, Andrew D. [1 ]
Martin, Stephen F. [1 ]
机构
[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
AMINO-THIOCARBAMATE CATALYST; ASYMMETRIC BROMOLACTONIZATION; OLEFINIC ACIDS; IODOLACTONIZATION; TRISIMIDAZOLINE; HALOCYCLIZATION; STRATEGIES;
D O I
10.1021/ja305117m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel bifunctional catalyst derived from BINOL has been developed that promotes the highly enantioselective bromolactonizations of a number of structurally distinct unsaturated acids. Like some known catalysts, this catalyst promotes highly enantioselective bromolactonizations of 4- and 5-aryl-4-pentenoic acids, but it also catalyzes the highly enantioselective bromolactonizations of 5-alkyl-4(Z)-pentenoic acids. These reactions represent the first catalytic bromolactonizations of alkyl-substituted olefinic acids that proceed via 5-exo mode cyclizations to give lactones in which new carbon-bromine bonds are formed at a stereogenic center with high enantioselectivity. We also disclose the first catalytic desymmetrization of a prochiral dienoic acid by enantioselective bromolactonization.
引用
收藏
页码:11128 / 11131
页数:4
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