Direct asymmetric catalytic 1,2-addition of RZnX to aldehydes promoted by AlMe3 and reversal of expected stereochemistry

Jonathan Shannon; David Bernier; Daniel Rawson; Simon Woodward

doi:10.1039/b710681e

Direct asymmetric catalytic 1,2-addition of RZnX to aldehydes promoted by AlMe3 and reversal of expected stereochemistry

Chem Commun (Camb). 2007 Oct 14:(38):3945-7. doi: 10.1039/b710681e. Epub 2007 Aug 15.

Authors

Jonathan Shannon¹, David Bernier, Daniel Rawson, Simon Woodward

Affiliation

¹ School of Chemistry, The University of Nottingham, Nottingham, UKNG7 2RD.

PMID: 17896041
DOI: 10.1039/b710681e

Abstract

Addition of AlMe3 to commercial THF solutions of RZnX (R = aryl, functionalised aryl, vinyl; X = Br, I) simultaneously promotes Schlenk equilibria (leading to competent nucleophiles) and the formation of an Al-Zn-ligand catalyst delivering 80-90% ee for Ar(1)CH(OH)Ar(2) formation from aldehydes.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Aluminum / chemistry*
Bromides / chemistry
Catalysis
Iodides / chemistry
Molecular Conformation
Organometallic Compounds / chemistry*
Zinc Compounds / chemistry*

Substances

Aldehydes
Bromides
Iodides
Organometallic Compounds
Zinc Compounds
Aluminum