Phosphane-Catalyzed [3+2] Cycloaddition Reaction of Allenoate and Cyclic Imines: A Simple and Efficient Method for Synthesis of Benzo-Fused Cyclic Sulfamidate Heterocycles

Autor:	Jin Zhao, Yongna Zhang, You-Qing Wang, Haina Dong, Jie Zhang
Rok vydání:	2013
Předmět:	chemistry.chemical_compound Trifluoromethyl Chemistry Organocatalysis Organic Chemistry Organic chemistry Physical and Theoretical Chemistry Cycloaddition Catalysis
Zdroj:	European Journal of Organic Chemistry. 2013:3764-3770
ISSN:	1434-193X
DOI:	10.1002/ejoc.201201756
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ed107bde43aa193d508562e16a70dd3b https://doi.org/10.1002/ejoc.201201756 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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