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Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines
Author(s) -
de Nanteuil Florian,
Waser Jérôme
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106255
Subject(s) - annulation , enol , catalysis , chemistry , computer science , organic chemistry , stereochemistry , combinatorial chemistry
With nitrogen too : The first catalytic [3+2] annulation of aminocyclopropanes with enol ethers is reported (see scheme; Phth=phthaloyl). The reaction worked with easily accessible phthalimidocyclopropanes using 5 mol % of SnCl 4 in nearly quantitative yields. Polysubstituted cyclopentylamines, which are often present in bioactive compounds, were obtained with high diastereoselectivity and enantiospecificity.