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Synthesis of N-Acyl-N,O-acetals Mediated by Titanium Ethoxide

Min Li, Bingling Luo, Qi Liu, Yumin Hu, A. Ganesan, Peng Huang* and Shijun Wen*

*Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Guangzhou 510060, China, Email: huangpengsysucc.org.cn, wenshjsysucc.org.cn

M. Li, B. Luo, Q. Liu, Y. Hu, A. Ganesan, P. Huang, S. Wen, Org. Lett., 2014, 16, 10-13.

DOI: 10.1021/ol4031155 (free Supporting Information)



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Abstract

Unusual N-Acyl-N,O-acetals are present in a number of bioactive natural products and  can act as a synthetic precursor to unstable reactive N-acylimines. Various N-acyl-N,O-acetals can be prepared under mild conditions mediated by titanium ethoxide (Ti(OEt)4). The method also offers a new strategy to make other O-alkyl-N,O-acetals.

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Key Words

N,O-acetals, alcoholysis, multicomponent reactions


ID: J54-Y2014