Chen, S;Mondal, M;Adams, MP;Wheeler, KA;Kerrigan, NJ

2015

November

Tetrahedron Letters

Phosphine-catalyzed synthesis of beta-lactones from ketenes and chiral beta-oxyaldehydes

Published

2 ()

MUKAIYAMA-ALDOL-LACTONIZATION ASYMMETRIC-SYNTHESIS DISUBSTITUTED KETENES POLYPROPIONATE SYSTEMS ALDEHYDES TRIBUTYLPHOSPHINE CYCLOADDITIONS (-)-PIRONETIN ASSEMBLAGE INDUCTION

56

6421

6424

In this Letter we describe a catalytic procedure for the diastereoselective synthesis of beta-lactones bearing up to three stereogenic centers, from disubstituted ketenes and chiral beta-oxyaldehydes. Tri-n-butylphosphine was determined to be the best catalyst with yields of up to 95% and moderate to good diastereos-electivity (dr up to 4:1) obtained in the formation of highly substituted beta-lactones. (C) 2015 Elsevier Ltd. All rights reserved.

OXFORD

0040-4039

10.1016/j.tetlet.2015.09.141