Issue 61, 2016

l-Isoleucine derived bifunctional phosphine catalyses asymmetric [3 + 2]-annulation of allenyl-esters and -ketones with ketimines

Abstract

The zwitterionic 1,3-dipoles generated by the addition of a bifunctional L-isoleucine derived N-acylaminophosphine to allenic esters as well as ketones were successfully trapped with isatin derived ketimines in a [3 + 2]-annulation reaction to deliver 3,2′-dihydropyrrolyl spirooxindoles in high yields (up to 88%) and with excellent enantioselectivities (up to >99%). The asymmetric annulation reaction provides a facile access to biologically relevant small molecules embodying the natural product spirocyclic core.

Graphical abstract: l-Isoleucine derived bifunctional phosphine catalyses asymmetric [3 + 2]-annulation of allenyl-esters and -ketones with ketimines

Supplementary files

Article information

Article type
Paper
Submitted
12 พ.ค. 2559
Accepted
07 มิ.ย. 2559
First published
08 มิ.ย. 2559

RSC Adv., 2016,6, 56537-56543

L-Isoleucine derived bifunctional phosphine catalyses asymmetric [3 + 2]-annulation of allenyl-esters and -ketones with ketimines

M. G. Sankar, M. Garcia-Castro, C. Golz, C. Strohmann and K. Kumar, RSC Adv., 2016, 6, 56537 DOI: 10.1039/C6RA12387B

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