The organocatalyzed asym. aza-Michael addn. of hydrazones to cyclic enones has been achieved in good yield and stereoselection using cheap and com. available cinchona alkaloids as catalysts. A systematic study of the influence of the structure of the enone on the stereoselectivity was carried out, leading to optically active products with up to 77% ee. The products can be recrystd. to give nearly enantiopure products, and furthermore it was shown that the products could be reduced to the corresponding 1,3-benzylidenehydrazino alc. derivs. with high diastereoselectivity.
Asymmetric Aza-Michael Reactions Catalyzed by Cinchona Alkaloids / D. Perdicchia, K.A. Jorgensen. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 72:9(2007), pp. 3565-3568.
Titolo: | Asymmetric Aza-Michael Reactions Catalyzed by Cinchona Alkaloids |
Autori: | PERDICCHIA, DARIO (Primo) |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 2007 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/jo0626717 |
Appare nelle tipologie: | 01 - Articolo su periodico |