Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates.
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.
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Gamal A I
GA
Moustafa
Yasumasa
Y
Kamada
Tetsuaki
T
Tanaka
Takehiko
T
Yoshimitsu
D000478:Alkylation; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D006840:Hydrocarbons, Alicyclic / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D006840:Hydrocarbons, Alicyclic