Lewis Base-Catalyzed Allylic Alkylation of α-Amino Nitriles and Cyanohydrins and Synthetic Applications

doi:10.6023/cjoc201406038

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2187-2194.DOI: 10.6023/cjoc201406038 Previous Articles Next Articles

Lewis碱催化的α-胺基腈及氰醇的烯丙基官能团化反应研究及应用

秦天游^a,b, 张晓安^a,b, 寮渭巍^b

a 大连理工大学精细化工国家重点实验室大连 116024;
b 吉林大学化学学院长春 130012

收稿日期:2014-06-23 修回日期:2014-08-03 发布日期:2014-08-11
通讯作者: 寮渭巍,wliao@jlu.edu.cn E-mail:wliao@jlu.edu.cn
基金资助:
国家自然科学基金(No.21372096)资助项目.

Lewis Base-Catalyzed Allylic Alkylation of α-Amino Nitriles and Cyanohydrins and Synthetic Applications

Qin Tianyou^a,b, Zhang Sean Xiao-An^a,b, Liao Weiwei^b

a State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024;
b Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012

Received:2014-06-23 Revised:2014-08-03 Published:2014-08-11
Supported by:
Project supported by the National Natural Science Foundation of China (No.21372096).

Abstract

This article summarized our recent progress in Lewis base-catalyzed the direct allylic substitutions of Morita-Baylis-Hillman (MBH) adducts with α-amino nitriles and cyanohydrins bearing an α-hydrogen, which provided efficient access to functionalized α-amino nitriles and cyanohydrins incorporating quaternary carbon centers. On the basis of these, a novel metal-free carbocyanation (alkenylcyanation and acylcyanation) approach to construct functionalized nitriles incorporating β-quaternary carbon center has been developed. In addition, the several factors influencing these chemical transformations are discussed, and the possible mechanism is proposed.

Key words: allylic alkylation, Lewis base, catalysis, α-amino nitriles, cyanohydrins, carbocyanation

Cite this article

Qin Tianyou, Zhang Sean Xiao-An, Liao Weiwei. Lewis Base-Catalyzed Allylic Alkylation of α-Amino Nitriles and Cyanohydrins and Synthetic Applications[J]. Chin. J. Org. Chem., 2014, 34(11): 2187-2194.

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Lewis碱催化的α-胺基腈及氰醇的烯丙基官能团化反应研究及应用

Lewis Base-Catalyzed Allylic Alkylation of α-Amino Nitriles and Cyanohydrins and Synthetic Applications

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