Use of Odorless Thiols: Formal Asymmetric Michael Addition of Hydrogen Sulfide to α-Substituted α,β-Unsaturated Carbonyl Compounds
- 31 August 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (20) , 3121-3124
- https://doi.org/10.1021/ol016406d
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
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