Formation of Macrocyclic Lactones by Enantioselective Intramolecular Cyclopropanation of Diazoacetates Catalyzed by Chiral Cu  I   and Rh  II   Compounds | Zendy

Doyle Michael P. | Zendy; Peterson Chad S. | Zendy; Parker Dann L. | Zendy

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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 ).

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