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

Patra, Atanu ; Bhunia, Anup ; Yetra, Santhivardhana Reddy ; Gonnade, Rajesh G. ; Biju, Akkattu T. (2015) Diastereoselective synthesis of cyclopentanone-fused spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes Organic Chemistry Frontiers, 2 (12). pp. 1584-1588. ISSN 2052-4129

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Official URL: http://doi.org/10.1039/C5QO00242G

Related URL: http://dx.doi.org/10.1039/C5QO00242G

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 spiro-heterocyclic 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.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry
ID Code:128670
Deposited On:03 Nov 2022 06:52
Last Modified:03 Nov 2022 06:52

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