期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2013, 期 18, 页码 3764-3770出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201756
关键词
Allenes; Cyclic sulfamidates; Cycloaddition; Organocatalysis; Phosphanes; Heterocycles
资金
- National Natural Science Foundation of China [21002022]
- Chinese Ministry of Education (the Scientific Research Foundation for the Returned Overseas Chinese Scholars)
- postdoctoral science foundation supports of Henan province in China
By using a phosphane as an organocatalyst, an efficient synthesis of benzo-fused cyclic sulfamidate heterocycles has been developed through a cycloaddition reaction of allenoate and cyclic imines including cyclic trifluoromethyl ketimine, which gave high yields (71-97%). The reaction could also be conveniently performed on a gram scale. Furthermore, some simple transformations of the sulfamidate heterocycle products have been disclosed to obtain functional amines. An asymmetric variant of this reaction was also tried by screening several commercially available chiral phosphane ligands as organocatalysts, and up to 36% ee was achieved.
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