- Stereochemistry of the Michael Addition of N,N-Disubstituted Amide and Thioamide Enolates to α,β-Unsaturated Ketones
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A systematic study of the regio- and diastereoselectivity of the kinetic Michael addition of amide and thioamide enolates to a series of α,β-unsaturated ketones has been carried out.Factors that influence the diastereo- and regiochemical outcome of the reaction include the substitution pattern of the enone and enolate, the enolate counterion, and the solvent.Numerous examples of high selectivity have been discovered.In a number of examples, either the syn or the anti addition products can be obtained by varying the nature of the solvent, donor atom, and/or counterion.These results have correlated in terms of a coherent transition-state model.
- Oare, David A.,Henderson, Mark A.,Sanner, Mark A.,Heathcock, Clayton H.
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p. 132 - 157
(2007/10/02)
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