title: Use of odorless thiols: formal asymmetric Michael addition of hydrogen sulfide to alpha-substituted alpha,beta-unsaturated carbonyl compounds.
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.
authors.affiliation: Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Nishide
authors.lastname: Ohsugi Si
authors.forename: H
authors.initials: H
authors.lastname: Shiraki
authors.forename: H
authors.initials: H
authors.lastname: Tamakita
authors.forename: M
authors.initials: M
authors.lastname: Node