Download PDF
Synthesis 1995; 1995(4): 458-472
DOI: 10.1055/s-1995-4429
feature article
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of Enantiomerically Pure Eight- and Nine-Membered Lactones by Copper(I) Chloride/2,2’-Bipyridine-Catalyzed Cyclization

Frank O.H. Pirrung, Henk Hiemstra* , W. Nico Speckamp1 , Bernard Kaptein, Hans E. Schoemaker
  • *Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands, Fax +31(20)5255670
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The stereocontrolled formation of eight- and nine-membered lactones by Cu(I)Cl/2,2’-bipyridine-catalyzed atom transfer cyclization of enantiomerically pure oxygen-substituted ω-alkenyl di- and trichloroacetates is described. The lactones are formed exclusively via the endo-cyclization mode and generally show a characteristic cis-relationship between the C-5 and C-6 substituents due to a highly stereoselective ring closure and chlorine transfer.

chiral pool - copper catalyst - stereoselective chlorine transfer cyclization - enantiopure lactones