ASYMMETRIC-SYNTHESIS OF MULTIFUNCTIONAL CYCLOPENTANES AND CYCLOHEXANES VIA OXYCARBENIUM ION CYCLIZATIONS OF 5-ALKOXY-2(3H)-DIHYDROFURANONES

Authors
GEERTSEMA EM LEUNG CW VANOEVEREN A MEETSMA A FERINGA BL
Citation
Em. Geertsema et al., ASYMMETRIC-SYNTHESIS OF MULTIFUNCTIONAL CYCLOPENTANES AND CYCLOHEXANES VIA OXYCARBENIUM ION CYCLIZATIONS OF 5-ALKOXY-2(3H)-DIHYDROFURANONES, Tetrahedron letters, 36(40), 1995, pp. 7315-7318
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
40
Year of publication
1995
Pages
7315 - 7318
Database
ISI
SICI code
0040-4039(1995)36:40<7315:AOMCAC>2.0.ZU;2-#
Abstract
Intramolecular nucleophilic additions to oxycarbenium ions derived fro m 5-alkoxy-2(3)-dihydrofuranones gave substituted cyclopentanes or cyc lohexanes in good yields. Stereoselectivity in these reactions was usu ally very high, while regioselectivity could be improved using silicon containing nucleophiles.