A highly efficient asymmetric synthesis of optically active alpha, gamma-substituted gamma-butyrolactones using a chiral auxiliary derived from isosorbide

M H Xu; W Wang; G Q Lin

doi:10.1021/ol005978f

A highly efficient asymmetric synthesis of optically active alpha, gamma-substituted gamma-butyrolactones using a chiral auxiliary derived from isosorbide

Org Lett. 2000 Jul 27;2(15):2229-32. doi: 10.1021/ol005978f.

Authors

M H Xu¹, W Wang, G Q Lin

Affiliation

¹ Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenlin Lu, Shanghai 200032, P. R. China.

PMID: 10930250
DOI: 10.1021/ol005978f

Abstract

Using an easily accessible and inexpensive chiral auxiliary derived from isosorbide, optically active alpha,gamma-substituted gamma-butyrolactones were obtained in high enantiomeric purity (up to >99% ee for trans) by the SmI(2)-induced reductive coupling of chiral methacrylate 7 with ketones in the presence of (-)-sultam as a proton source.

Publication types

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

MeSH terms

4-Butyrolactone / chemical synthesis*
4-Butyrolactone / chemistry
4-Butyrolactone / metabolism
Isosorbide / chemistry*
Isosorbide / metabolism*
Ketones / metabolism
Methacrylates / metabolism
Protons
Stereoisomerism*

Substances

Ketones
Methacrylates
Protons
4-Butyrolactone
Isosorbide