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Synthesis 1995; 1995(4): 458-472
DOI: 10.1055/s-1995-4429
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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
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Publication Date:
31 December 2000 (online)

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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

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