Issue 47, 2021

Enantioselective organocatalytic formal [3+2]-cycloaddition of isatin-derived ketimines with benzylidenemalononitriles and benzylidineindanones

Abstract

The biological and medicinal importance of oxindole-derived spirocycles is now well-established, and has inspired the development of numerous creative synthetic strategies. Here we report an efficient formal [3+2]-cycloaddition of isatin-derived N-trifluoroethyl ketimines with a series of benzylidinemalononitrile and benzylidineindandione dipolarophiles catalysed by a cinchona-derived thiourea catalyst. The reaction affords a series of functionalized spiro-pyrrolidinoxindole products with up to four contiguous stereocentres in excellent yields, ee and d.r. (up to 98% yield, 97% ee, and >100 : 1 d.r.). These products share a common core scaffold with compounds previously found to have anti-tumour, anti-microbial and anti-inflammatory activities.

Graphical abstract: Enantioselective organocatalytic formal [3+2]-cycloaddition of isatin-derived ketimines with benzylidenemalononitriles and benzylidineindanones

Supplementary files

Article information

Article type
Communication
Submitted
20 Aug 2021
Accepted
23 Oct 2021
First published
03 Nov 2021

New J. Chem., 2021,45, 22034-22038

Enantioselective organocatalytic formal [3+2]-cycloaddition of isatin-derived ketimines with benzylidenemalononitriles and benzylidineindanones

C. Duffy, W. E. Roe, A. M. Harkin, R. McNamee and P. C. Knipe, New J. Chem., 2021, 45, 22034 DOI: 10.1039/D1NJ04002B

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