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

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• 作者：Karimulla Mulla ; Kyle L. Aleshire ; Paul M. Forster ; Jun Yong Kang
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：January 4, 2016
• 年：2016
• 卷：81
• 期：1
• 页码：77-88
• 全文大小：686K
• ISSN：1520-6904

文摘

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.