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Organoselenium-Catalyzed, Hydroxy-Controlled Regio- and Stereoselective Amination of Terminal Alkenes: Efficient Synthesis of 3-Amino Allylic Alcohols

Zhimin Deng, Jialiang Wei, Lihao Liao, Haiyan Huang and Xiaodan Zhao*

*Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, PR China, Email: zhaoxd3mail.sysu.edu.cn

Z. Deng, J. Wei, L. Liao, H. Huang, X. Zhao, Org. Lett., 2015, 17, 1834-1837.

DOI: 10.1021/acs.orglett.5b00213 (free Supporting Information)


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Abstract

Orangoselenium catalysis enables an efficient route to 3-amino allylic alcohols in excellent regio- and stereoselectivity in the presence of a base. In the absence of bases α,β-unsaturated aldehydes were formed in excellent yield. The hydroxy group is crucial for the direct amination.

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Key Words

sulfonamides, enamines, enones, NFSI


ID: J54-Y2015