Asymmetric vinylogous michael reaction of cyclic enones with silyloxy furans

TitleAsymmetric vinylogous michael reaction of cyclic enones with silyloxy furans
Publication TypeJournal Article
Year of Publication2015
AuthorsJadhav, AP, Rao, VUBhaskar, Singh, P, Gonnade, RG, Singh, RP
JournalChemical Communications
Volume51
Issue73
Pagination13941-13944
Date PublishedJUL
ISSN1359-7345
Abstract

The asymmetric vinylogous Michael reaction of cyclohexenone/medium and large cyclic enones with 2-silyloxyfuran is still a synthetic challenge. In this report, we have explored 1,4-conjugate addition of an enantioselective chiral, primary diamine catalyzed, 2-silyloxy furan to various cyclic enones and beta-substituted cyclic enones. The reaction provided syn-Michael adducts (cycloalkane connected gamma-butenolide) with good yields, diastereo and enantioselectivities. Furthermore, the synthetic potential of these syn-Michael adducts is demonstrated by 1,4-addition of nucleophiles on the butenolide substructure.

DOI10.1039/c5cc05617a
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.567

Divison category: 
Center for Material Characterization (CMC)