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 journalArticle

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 languageEnglish
Pages (from-to)1202-1207
Number of pages6
JournalJournal of Organic Chemistry
Volume77
Issue number2
DOIs
Publication statusPublished - Jan 20 2012
Externally publishedYes

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Alkylation
Chelation
Hydroxyl Radical
alkoxyl radical

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates. / Moustafa, Gamal A I; Kamada, Yasumasa; Tanaka, Tetsuaki; Yoshimitsu, Takehiko.

In: Journal of Organic Chemistry, Vol. 77, No. 2, 20.01.2012, p. 1202-1207.

Research output: Contribution to journalArticle

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