Jump to Main Content
Utility of Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas for Metal-Free Carbon–Phosphorus Bond Construction toward Regio- and Stereoselective Formation of Vinylphosphonates
- Mulla, Karimulla, Aleshire, Kyle L., Forster, Paul M., Kang, Jun Yong
- Journal of organic chemistry 2016 v.81 no.1 pp. 77-88
- Lewis bases, chemical reactions, heterocyclic nitrogen compounds, moieties, organic chemistry, phosphine, regioselectivity, stereoselective synthesis, stereoselectivity
- 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.