Three-Component Glycolate Michael Reactions of Enolates, Silyl Glyoxylates, and α,β-Enones
The Journal of Organic Chemistry2012Vol. 77(7), pp. 3246–3251
Citations Over TimeTop 14% of 2012 papers
Abstract
Silyl glyoxylates react with enolates and enones to afford either glycolate aldol or Michael adducts. Product identity is controlled by the countercation associated with the enolate. Reformatsky nucleophiles in the presence of additional Zn(OTf)(2) result in aldol coupling (A), while lithium enolates provide the Michael coupling (B). Deprotonation of the aldol product A with LDA induces equilibration to form the minor diastereomer of Michael product B. This observation suggests that formation of the major diastereomer of Michael product B does not occur via an aldol/retro-aldol/Michael sequence.
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