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Macrocyclic Cyclopropenes by Highly Enantioselective Intramolecular Addition of Metal Carbenes to Alkynes
Author(s) -
Doyle Michael P.,
Ene Doina G.,
Peterson Chad S.,
Lynch Vince
Publication year - 1999
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/(sici)1521-3773(19990301)38:5<700::aid-anie700>3.0.co;2-3
Subject(s) - intramolecular force , enantioselective synthesis , chemoselectivity , chemistry , diazo , ring (chemistry) , triple bond , catalysis , medicinal chemistry , stereochemistry , combinatorial chemistry , double bond , organic chemistry
The intramolecular addition of a diazo ester group to a triple bond in the presence of chiral dirhodium( II ) carboxamidate catalysts gives macrocyclic lactones with a fused cycloproprene ring [Eq. (a)]. This efficient reaction is characterized by high enantiocontrol (up to 98% ee ) and chemoselectivity.