Iterative approach to enantiopure syn/anti-1,3-polyols via proline-catalyzed sequential alpha-aminoxylation and horner-wadsworth-emmons olefination of aldehydes

TitleIterative approach to enantiopure syn/anti-1,3-polyols via proline-catalyzed sequential alpha-aminoxylation and horner-wadsworth-emmons olefination of aldehydes
Publication TypeJournal Article
Year of Publication2009
AuthorsKondekar, NB, Kumar, P
JournalOrganic Letters
Volume11
Issue12
Pagination2611-2614
Date PublishedJUN
ISSN1523-7060
Abstract

Iterative use of proline-catalyzed tandem alpha-aminoxylation and HWE olefination of aldehydes provided a simple access to 1,3-polyols. The feasibility of this approach is initially studied to synthesize syn- and anti-1,3-diols and is further extended to a syn/syn-1,3,5-triol at a useful level of asymmetric induction and yield. Its usage is Illustrated by the short synthesis of a hydroxylactone pheromone component, (2S,3S)-2-hydroxyhexylcyclopentanone.

DOI10.1021/ol900868v
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)5.250
Divison category: 
Organic Chemistry