TY - JOUR
T1 - Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates
AU - Moustafa, Gamal A.I.
AU - Kamada, Yasumasa
AU - Tanaka, Tetsuaki
AU - Yoshimitsu, Takehiko
N1 - Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.
PY - 2012/1/20
Y1 - 2012/1/20
N2 - 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.
AB - 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.
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U2 - 10.1021/jo2022789
DO - 10.1021/jo2022789
M3 - Article
C2 - 22208771
AN - SCOPUS:84862973846
VL - 77
SP - 1202
EP - 1207
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 2
ER -