UNEXPECTED SELECTIVITY BETWEEN PINACOLIC REARRANGEMENT AND INTRAMOLECULAR DISPLACEMENT IN THE ACID-PROMOTED EPOXIDE RING-OPENING OF -CYANO-3,8-DIOXABICYCLO[3.2.1.0(2,4)]OCT-6-ENDO-YL ESTERS

Authors
ALLEMANN S VOGEL P
Citation
S. Allemann et P. Vogel, UNEXPECTED SELECTIVITY BETWEEN PINACOLIC REARRANGEMENT AND INTRAMOLECULAR DISPLACEMENT IN THE ACID-PROMOTED EPOXIDE RING-OPENING OF -CYANO-3,8-DIOXABICYCLO[3.2.1.0(2,4)]OCT-6-ENDO-YL ESTERS, Tetrahedron, 50(8), 1994, pp. 2469-2478
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
8
Year of publication
1994
Pages
2469 - 2478
Database
ISI
SICI code
0040-4020(1994)50:8<2469:USBPRA>2.0.ZU;2-C
Abstract
Acid promoted epoxide ring opening of exo,6-exo-epohy-7-oxa-bicyclo[2. 2.1]hept-2-endo-yl acetate is accompanied by a Wagnet-Meerwein (pinaco lic) rearrangemant when run in CH2Cl2/HSO3-F and by endo acetoxy group participation when run in CF3CH(OH)CF3/HClO4. An efficient and stereo selective trans-double hydroxylation of centers C(5) and C(6) of the ' 'naked sugar'' ,4R)-2-exo-cyano-7-oxabicyclo[2.2.1]hept-2-endo-yl (1S' )-camphanate is also presented.