STERIC CONTROL-BASED ON ALKYL SUBSTITUENTS IN THE [2,3]SIGMATROPIC REARRANGEMENT OF 9-MEMBERED ALLYLSULFONIUM YLIDES - A NEW ENTRY TO THE STEREOSELECTIVE SYNTHESIS OF ELEMANE-TYPE SESQUITERPENOIDS

Authors
KIDO F YAMAJI K SINHA SC YOSHIKOSHI A KATO M
Citation
F. Kido et al., STERIC CONTROL-BASED ON ALKYL SUBSTITUENTS IN THE [2,3]SIGMATROPIC REARRANGEMENT OF 9-MEMBERED ALLYLSULFONIUM YLIDES - A NEW ENTRY TO THE STEREOSELECTIVE SYNTHESIS OF ELEMANE-TYPE SESQUITERPENOIDS, Journal of the Chemical Society, Chemical Communications, (7), 1994, pp. 789-790
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
7
Year of publication
1994
Pages
789 - 790
Database
ISI
SICI code
0022-4936(1994):7<789:SCOASI>2.0.ZU;2-L
Abstract
The rhodium(II)-catalysed cyclisation of acyclic alpha-diazomalonate 1 b and alpha-diazo-beta-keto esters 1c, d give stereoselectively the hi ghly substituted delta-lactone 3b and cyclohexanones 3c, d, respective ly, by [2,3]sigmatropic rearrangement via the stereocontrolled nine-me mbered allylsulfonium ylides 2b-d.