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Formation of Macrocyclic Lactones by Enantioselective Intramolecular Cyclopropanation of Diazoacetates Catalyzed by Chiral Cu I and Rh II Compounds
Author(s) -
Doyle Michael P.,
Peterson Chad S.,
Parker Dann L.
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199613341
Subject(s) - cyclopropanation , intramolecular force , enantioselective synthesis , ring (chemistry) , catalysis , regioselectivity , chemistry , stereochemistry , ligand (biochemistry) , medicinal chemistry , organic chemistry , receptor , biochemistry
A new method for the catalytic asymmetric synthesis of macrocycles is based on the intramolecular cyclopropanation of long‐chain diazoacetates containing a double bond. Thus, for example, with [Cu(MeCN) 4 ](PF 6 ) in the presence of a chiral bis(dihydrooxazole) ligand, the 15‐membered ring lactone 1 was formed not only with excellent regioselectivity (ratio of 15‐membered to 10‐membered ring is 25:1) but also with remarkably high enantioselectivity (90% ee ).