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

J Org Chem. 2012 Jan 20;77(2):1202-7. doi: 10.1021/jo2022789. Epub 2012 Jan 11.

Authors

Gamal A I Moustafa¹, Yasumasa Kamada, Tetsuaki Tanaka, Takehiko Yoshimitsu

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 22208771
DOI: 10.1021/jo2022789

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Chemistry Techniques, Synthetic / methods*
Hydrocarbons, Alicyclic / chemical synthesis
Hydrocarbons, Alicyclic / chemistry*
Molecular Structure
Stereoisomerism

Substances

Hydrocarbons, Alicyclic