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Synthesis of Stereohomogeneous Cyclopropanecarbaldehydes and Cyclopropyl Ketones by Cycloalkylation of 4‐Hydroxy‐1‐alkenyl Carbamates
Author(s) -
Kalkofen Rainer,
Brandau Sven,
Wibbeling Birgit,
Hoppe Dieter
Publication year - 2004
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.200461136
Subject(s) - cyclopropane , chemistry , intramolecular force , alkylation , ketone , organic chemistry , stereochemistry , ring (chemistry) , catalysis
Small rings : Only a few methods are known for the synthesis of cyclopropane carbaldehydes and cyclopropyl ketones 2 . In a new, simple route to highly enantioenriched trisubstituted three‐membered rings, 4‐hydroxy‐1‐alkenyl N , N ‐diisopropyl carbamates 1 are treated with NaH, resulting in migration of the carbamoyl group and intramolecular enolate alkylation.