Efficient synthesis of α-amino-vinylphosphine oxides from alkyl nitriles via manganese-catalyzed phosphinoenamination

Runbo Sun; Yang Junpeng; Zheng Zhang; Ruihang Luo; Wentao Tang; Xinyu Liu; Xiaoyong Liu; Anjun Ding; Zhengjiang Fu; Shengmei Guo; Hu Cai

doi:10.1039/D4OB00489B

Efficient synthesis of α-amino-vinylphosphine oxides from alkyl nitriles via manganese-catalyzed phosphinoenamination†

Runbo Sun,^a Yang Junpeng,^a Zheng Zhang,^b Ruihang Luo,^b Wentao Tang,^b Xinyu Liu,^b Xiaoyong Liu,^a Anjun Ding,^a Zhengjiang Fu,

^a Shengmei Guo

*^a and Hu Cai

*^a

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* Corresponding authors

^a Department of Chemistry, Nanchang University, Xuefu Rd. 999, Nanchang, P. R. China
E-mail: smguo@ncu.edu.cn, caihu@ncu.edu.cn

^b The First Clinical Medical College, Nanchang University, Xuefu Rd. 999, Nanchang, P. R. China

Abstract

A protocol for the synthesis of α-amino-vinylphosphine oxides by phosphinoenamination reaction between alkyl nitriles and phosphine oxides was developed. The combination of Mn(OAc)₂ as a Lewis acid and guanidine as a Lewis base was found to be an efficient catalytic system for this reaction. A series of alkyl nitriles and phosphine oxides are compatible with this conversion, furnishing the desired products in up to 95% yield under mild conditions. Furthermore, this method demonstrates the capability of gram-scale synthesis.

Organic & Biomolecular Chemistry

Efficient synthesis of α-amino-vinylphosphine oxides from alkyl nitriles via manganese-catalyzed phosphinoenamination†

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Efficient synthesis of α-amino-vinylphosphine oxides from alkyl nitriles via manganese-catalyzed phosphinoenamination

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