Utility of Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas for Metal-Free Carbon–Phosphorus Bond Construction toward Regio- and Stereoselective Formation of Vinylphosphonates

Authors

Karimulla MullaFollow
Kyle L. AleshireFollow
Paul M. Forster, University of Nevada, Las VegasFollow
Jun Yong Kang, University of Nevada, Las VegasFollow

Document Type

Article

Publication Date

1-4-2016

Publication Title

The Journal of Organic Chemistry

Volume

81

Issue

1

First page number:

77

Last page number:

88

Abstract

An efficient and practical protocol for completely regioselective and highly stereoselective synthesis of vinyldiazaphosphonates from N-heterocyclic phosphine (NHP) and allenes via phospha-Michael/intramolecular nucleophilic substitution reaction has been developed. This transformation enabled the synthesis of valuable densely functionalized vinyldiazaphosphonates with a β-, γ-unsaturated ester moiety under mild reaction conditions. Synthetic utility of vinyldiazaphosphonates was demonstrated by a series of synthetic manipulations.

Repository Citation

Mulla, K., Aleshire, K. L., Forster, P. M., Kang, J. Y. (2016). Utility of Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas for Metal-Free Carbon–Phosphorus Bond Construction toward Regio- and Stereoselective Formation of Vinylphosphonates. The Journal of Organic Chemistry, 81(1), 77-88.
http://dx.doi.org/10.1021/acs.joc.5b02184