Journal of Organic Chemistry 2012-01-20

Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates.

Gamal A I Moustafa, Yasumasa Kamada, Tetsuaki Tanaka, Takehiko Yoshimitsu

Index: J. Org. Chem. 77(2) , 1202-7, (2012)

Full Text: HTML

Abstract

The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3'-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the α-quaternization possibly implies intervention of a rigid chelating transition state that allows an efficient 1,4-asymmetric induction to take place.