STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .42. STEREOSELECTIVE CYCLIZATION OF (8-OXO-2-OCTENYL)BORONATES TO CIS-2-VINYLCYCLOHEXANOL OR TRANS-2-VINYLCYCLOHEXANOL

Authors
HOFFMANN RW SANDER T HENSE A
Citation
Rw. Hoffmann et al., STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .42. STEREOSELECTIVE CYCLIZATION OF (8-OXO-2-OCTENYL)BORONATES TO CIS-2-VINYLCYCLOHEXANOL OR TRANS-2-VINYLCYCLOHEXANOL, Liebigs Annalen der Chemie, (7), 1993, pp. 771-775
Citations number
43
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen der Chemie → ACNP
ISSN journal
01702041
Issue
7
Year of publication
1993
Pages
771 - 775
Database
ISI
SICI code
0170-2041(1993):7<771:SSOA.S>2.0.ZU;2-1
Abstract
Intramolecular allylboration reactions of (8-oxo-2-octenyl)boronates p roceed with excellent diastereoselectivity: the E-isomer 1d leads to t he trans-2-vinylcyclohexanol (2) with 99.5% d.s., the corresponding Z- isomer 3d cyclizes to give the cis-isomer with a diastereoselectivity exceeding 99.8%.