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. 2018 Apr 24;8(28):15444-15447.
doi: 10.1039/c8ra02009d. eCollection 2018 Apr 23.

A C1-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones

Jun-Bing Lin  1 , Xi-Na Cheng  1 , Xiao-Dong Tian  1 , Guo-Qiang Xu  1 , Yong-Chun Luo  1 , Peng-Fei Xu  1
Affiliations

A C1-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones

Jun-Bing Lin et al. RSC Adv. .

Abstract

A C1-symmetric N-heterocyclic carbene (NHC)-catalysed activation of isatin-derived enals under oxidative conditions was achieved. The in situ generated α,β-unsaturated acyl azolium species was efficiently trapped by 1,3-dicarbonyl compounds via a Michael addition/spiroannualtion cascade, delivering a series of synthetically important spirooxindole δ-lactones with up to 96% enantioselectivity.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. (a) Examples of spirooxindole-containing natural products. (b) Assembly of spirooxindole δ-lactone scaffolds via C1-symmetric NHC-catalysed spiroannulation (this work).
Scheme 1
Scheme 1. Proposed catalytic cycle.
See this image and copyright information in PMC

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