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: ybkang
ustc.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
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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
