Issue 31, 2019

Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones

Abstract

The highly efficient addition of phosphorus and carbon pronucleophiles to α-methylene-γ-butyrolactones (tulipalin A and arglabin) under n-Bu3P catalysis is reported. Kinetic experiments indicate that the unprecedentedly high reactivity of α-methylene-γ-butyrolactones results from the rigid s-cis geometry of the 1-oxa-1,3-butadiene moiety that favors generation of zwitterionic intermediate stabilized by interaction between the phosphonium center and adjacent carbonyl oxygen. The presented strategy offers an economical and practical method for functionalization of natural biologically active α-methylene-γ-butyrolactones with high levels of chemo- and stereoselectivity.

Graphical abstract: Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones

Supplementary files

Article information

Article type
Communication
Submitted
21 Jun 2019
Accepted
10 Jul 2019
First published
15 Jul 2019

Org. Biomol. Chem., 2019,17, 7293-7299

Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones

A. V. Salin and D. R. Islamov, Org. Biomol. Chem., 2019, 17, 7293 DOI: 10.1039/C9OB01401B

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