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

Author:
Mulla, Karimulla, Aleshire, Kyle L., Forster, Paul M., Kang, Jun Yong
Source:
Journal of organic chemistry 2016 v.81 no.1 pp. 77-88
ISSN:
1520-6904
Subject:
Lewis bases, chemical reactions, heterocyclic nitrogen compounds, moieties, organic chemistry, phosphine, regioselectivity, stereoselective synthesis, stereoselectivity
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.
Agid:
5505423