SYNTHESIS OF ENANTIOMERICALLY PURE 8-MEMBERED AND 9-MEMBERED LACTONESBY COPPER(I) CHLORIDE 2,2'-BIPYRIDINE-CATALYZED CYCLIZATION CYCLIZATION

Authors
PIRRUNG FOH HIEMSTRA H SPECKAMP WN KAPTEIN B SCHOEMAKER HE
Citation
Foh. Pirrung et al., SYNTHESIS OF ENANTIOMERICALLY PURE 8-MEMBERED AND 9-MEMBERED LACTONESBY COPPER(I) CHLORIDE 2,2'-BIPYRIDINE-CATALYZED CYCLIZATION CYCLIZATION, Synthesis, (4), 1995, pp. 458-472
Citations number
75
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
4
Year of publication
1995
Pages
458 - 472
Database
ISI
SICI code
0039-7881(1995):4<458:SOEP8A>2.0.ZU;2-4
Abstract
The stereocontrolled formation of eight- and nine-membered lactones by Cu(I)Cl/2,2'-bipyridine-catalyzed atom transfer cyclization of enanti omerically pure oxygen-substituted omega-alkenyl di- and trichloroacet ates is described. The lactones are formed exclusively via the endo-cy clization mode and generally show a characteristic cis-relationship be tween the C-5 and C-6 substituents due to a highly stereoselective rin g closure and chlorine transfer.