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

doi:10.1021/jo2022789

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

Research output: Contribution to journal › Article

5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1202-1207
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	77
Issue number	2
DOIs	https://doi.org/10.1021/jo2022789
Publication status	Published - Jan 20 2012
Externally published	Yes

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ASJC Scopus subject areas

Organic Chemistry

Cite this

Moustafa, G. A. I., Kamada, Y., Tanaka, T., & Yoshimitsu, T. (2012). Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates. Journal of Organic Chemistry, 77(2), 1202-1207. https://doi.org/10.1021/jo2022789

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10.1021/jo2022789