H2O-Regulated Chemoselectivity in Oxa- Versus Aza-Michael Reactions
Rong Huang1,2, Zhihong Li1, Jianghui Yu1
1Shanghai Institute for Advanced Immunochemical Studies , ShanghaiTech University , 393 Middle Huaxia Road , Pudong , Shanghai 201210 , China.
Abstract:
A H2O-regulated chemoselective addition in oxa- and aza-Michael reactions for aminoalcohols and mixtures of structurally similar alcohols and amines was reported. The oxa-Michael reactions might be kinetically controlled, and the reactions to produce O-selective products were slowed by the addition of water. The electrophilicity of Michael acceptors and the steric hindrance of Michael donors also affect the ratios of O/N products. This method offers novel ideas over conventional metal-catalyzed or ligand-induced strategies.
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