REGIOCONTROLLED AND STEREOCONTROLLED ALKYLATIVE RING-OPENING OF UNSYMMETRICAL 8-OXABICYCLO[3.2.1]OCTENE SYSTEMS - SYNTHESIS OF HIGHLY SUBSTITUTED HYDROXYCYCLOHEPTENYL SULFONES

Authors
ARJONA O DEDIOS A PLUMET J
Citation
O. Arjona et al., REGIOCONTROLLED AND STEREOCONTROLLED ALKYLATIVE RING-OPENING OF UNSYMMETRICAL 8-OXABICYCLO[3.2.1]OCTENE SYSTEMS - SYNTHESIS OF HIGHLY SUBSTITUTED HYDROXYCYCLOHEPTENYL SULFONES, Tetrahedron letters, 34(46), 1993, pp. 7451-7454
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
46
Year of publication
1993
Pages
7451 - 7454
Database
ISI
SICI code
0040-4039(1993)34:46<7451:RASARO>2.0.ZU;2-Q
Abstract
The organolithium mediated bridge opening of unsymmetrically substitut ed 8-oxabicyclo[3.2.1]octene derivatives 6, 7, proceeds with complete regio- and stereoselectivity to afford highly functionalized hydroxycy cloheptenyl sulfones 10, 12 in high yields. It was also found possible to control the conjugate addition/beta-elimination sequence towards t he synthesis of adducts 8,9, 11.