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Synthesis of syn-1,3-Aminoalcohols via a Ru-Catalyzed N-Demethylative Rearrangement of Isoxazolidines and Its Application in a Three-Step Total Synthesis of HPA-12

Chuan-Zhi Yao, Zu-Feng Xiao, Xiao-Shan Ning, Jie Liu, Xiao-Wei Zhang and Yan-Biao Kang*

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email: ybkangustc.edu.cn

C.-Z. Yao, Z.-F. Xiao, X.-S. Ning, J. Liu, X.-W. Zhang, Y.-B. Kang, Org. Lett., 2014, 16, 5824-5826.

DOI: 10.1021/ol502956j (free Supporting Information)


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Abstract

A highly efficient ruthenium-catalyzed stereospecific N-demethylative rearrangement of isoxazolidines gives synthetically useful N-H-1,3-oxazinanes. 1,3-Oxazinanes are useful building blocks, which can be converted to N-H-1,3-aminoalcohols in a subsequent step.

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Key Words

N-Heterocycles, O-Heterocycles, Hemiaminals, Cleavage of Hemiaminals, 1,3-aminoalcohols


ID: J54-Y2014