Bifunctional catalyst promotes highly enantioselective bromolactonizations to generate stereogenic C-Br bonds |
| |
Authors: | Paull Daniel H Fang Chao Donald James R Pansick Andrew D Martin Stephen F |
| |
Institution: | Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA. |
| |
Abstract: | 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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|