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

• DOI: 10.1021/acs.orglett.5b00213
• Publication Date: 2015-04-07T18:48:19Z
• Authors: Zhimin Deng; Jialiang Wei; Lihao Liao; Haiyan Huang; Xiaodan Zhao
• Keywords: Allyl Compounds; Propanolamines; Molecular Structure; Organoselenium Compounds; Stereoisomerism; Alkenes; 01 natural sciences; Catalysis; Amination; 0104 chemical sciences

An efficient route to prepare 3-amino allylic alcohols in excellent regio- and stereoselectivity the presence of bases by orangoselenium catalysis has been developed. In absence α,β-unsaturated aldehydes were formed up 97% yield. Control experiments reveal that hydroxy group is crucial for direct amination.