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|
PERDICCHIA, DARIO (Primo)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2007|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1021/jo0626717|
|Appare nelle tipologie:||01 - Articolo su periodico|