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 › peer-review

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

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo2022789

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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.",

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AU - Kamada, Yasumasa

AU - Tanaka, Tetsuaki

AU - Yoshimitsu, Takehiko

PY - 2012/1/20

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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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