Issue 62, 2019

Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones

Abstract

A chiral phosphine-catalyzed tandem Michael addition of tryptamine-derived oxindoles to ynones has been developed, which provides facile access to a series of optically enriched spiro[pyrrolidine-3,3′-oxindole] compounds in good yields with good to excellent enantio- (up to 97% ee) and diastereoselectivities (up to 20 : 1 dr). Mechanistic studies indicate that this tandem reaction proceeds via an intermolecular aza-Michael/intramolecular Michael addition process.

Graphical abstract: Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones

Supplementary files

Article information

Article type
Communication
Submitted
07 Jun 2019
Accepted
03 Jul 2019
First published
04 Jul 2019

Chem. Commun., 2019,55, 9176-9179

Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones

T. Cong, H. Wang, X. Li, H. Wu and J. Zhang, Chem. Commun., 2019, 55, 9176 DOI: 10.1039/C9CC04357H

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