Enantioselective 1,4-additions of ClMeAl(CH=CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones

D Willcox; S Woodward; A Alexakis

doi:10.1039/c3cc48191c

Enantioselective 1,4-additions of ClMeAl(CH=CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones

Chem Commun (Camb). 2014 Feb 18;50(14):1655-7. doi: 10.1039/c3cc48191c.

Authors

D Willcox¹, S Woodward, A Alexakis

Affiliation

¹ School of Chemistry, The University of Nottingham, University Park, Nottingham, UK. [email protected].

PMID: 24400320
DOI: 10.1039/c3cc48191c

Abstract

Chloromethylvinyl alanes (E)-ClMeAl(CH=CHR) prepared directly from terminal alkynes undergo 1,4-addition to cyclohexenone and 3-methylcyclohexenone in moderate to good yield (30-70%) and good to excellent stereoselectivity (80-98% ee) using readily available copper(I) sources and chiral ligands.