Diastereoselective synthesis of cyclopentanone-fused spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes

TitleDiastereoselective synthesis of cyclopentanone-fused spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes
Publication TypeJournal Article
Year of Publication2015
AuthorsPatra, A, Bhunia, A, Yetra, SReddy, Gonnade, RG, Biju, AT
JournalOrganic Chemistry Frontiers
Volume2
Issue12
Pagination1584-1588
Date PublishedSEP
Abstract

N-Heterocyclic carbene (NHC)-catalyzed formal [3 + 2] annulation of α,β-unsaturated aldehydes with N-substituted isatilidenes resulting in the diastereoselective synthesis of cyclopentanone-fused spirooxindoles is demonstrated. Mechanistically, the reaction proceeds via the generation of homoenolate equivalent intermediates from NHC and enals, which on interception with isatilidenes afford spiroheterocyclic compounds bearing an all-carbon quaternary spiro-center in moderate to good yields and generally with high diastereoselectivity. Moreover, the functionalization of the spirooxindoles as well as the initial studies on the enantioselective version of this reaction are presented.

DOI10.1039/C5QO00242G
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.693

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry