Use of odorless thiols: formal asymmetric Michael addition of hydrogen sulfide to alpha-substituted alpha,beta-unsaturated carbonyl compounds |
| |
Authors: | Nishide K Ohsugi Si Shiraki H Tamakita H Node M |
| |
Institution: | Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan. |
| |
Abstract: | reaction: see text] The Michael addition to alpha-substituted alpha,beta-unsaturated esters and amides using complex A containing a chiral odorless thiol proceeded diastereoselectively. The Michael adducts were converted to beta-mercapto esters and amides via a Wagner-Meerwein rearrangement with boron trifluoride etherate and a thiol exchange reaction using odorless 1-dodecanethiol. This conversion constitutes a formal asymmetric Michael addition of hydrogen sulfide to alpha,beta-unsaturated carbonyl compounds using odorless thiols instead of the toxic hydrogen sulfide. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|