Highly diastereo- and enantioselective synthesis of monodifferentiated syn-1,2-diol derivatives through asymmetric transfer hydrogenation via dynamic kinetic resolution

Damien Cartigny; Kurt Püntener; Tahar Ayad; Michelangelo Scalone; Virginie Ratovelomanana-Vidal

doi:10.1021/ol101451s

Highly diastereo- and enantioselective synthesis of monodifferentiated syn-1,2-diol derivatives through asymmetric transfer hydrogenation via dynamic kinetic resolution

Org Lett. 2010 Sep 3;12(17):3788-91. doi: 10.1021/ol101451s.

Authors

Damien Cartigny¹, Kurt Püntener, Tahar Ayad, Michelangelo Scalone, Virginie Ratovelomanana-Vidal

Affiliation

¹ Laboratoire Charles Friedel, UMR 7223, ENSCP Chimie ParisTech, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France.

PMID: 20672834
DOI: 10.1021/ol101451s

Abstract

The first enantio- and diastereoselective approach to alpha-alkoxy-substituted syn-beta-hydroxyesters through highly efficient catalytic asymmetric transfer hydrogenation via dynamic kinetic resolution reactions from the corresponding racemic beta-ketoesters is described. In this atom-economical process, two contiguous stereogenic centers are generated simultaneously with an excellent diastereoselectivity (up to 99/1) and enantioselectivity (up to 99%), allowing a rapid access to a wide variety of aromatic and heteroaromatic monodifferentiated syn-1,2-diols.

Publication types

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

MeSH terms

Alcohols / chemical synthesis*
Alcohols / chemistry
Catalysis
Combinatorial Chemistry Techniques
Esters
Hydrogenation
Kinetics
Molecular Structure
Ruthenium / chemistry*
Stereoisomerism

Substances

Alcohols
Esters
Ruthenium