Asymmetric Michael reactions of aminocarbene complex anions

Autor:	Benjamin Alan Anderson, William D. Wulff, Annette Rahm
Rok vydání:	1993
Předmět:	Chemistry Synthon General Chemistry Biochemistry Medicinal chemistry Catalysis Adduct chemistry.chemical_compound Colloid and Surface Chemistry Amide Michael reaction Dimethyldioxirane Carbene Enone Carbanion
Zdroj:	Journal of the American Chemical Society. 115:4602-4611
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00064a023
Popis:	The first Michael addition reactions of the anions of aminocarbene complexes to α,β-unsaturated carbonyl compounds are reported. Unlike their corresponding amide enolates, these anions give exclusive 1,4-addition to a number of enones. For chiral complex 27, it was shown that the formation of the 1,4-addition product is not reversible and that the initial 1,4-addition is thus kinetically controlled. The anions of aminocarbene complexes are much more effective in this regard than the anions of alkoxycarbene complexes. It was demonstrated that aminocarbene complexes can serve as synthons for amides in Michael additions since the metal can be liberated from the Michael adducts to give amide products by oxidation with either DMSO or dimethyldioxirane
Databáze:	OpenAIRE
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