IONIC DIELS-ALDER REACTIONS OF HEXA-3,5-DIENYL TRIMETHYLSILYL ETHER AND ENONES - X-RAY STRUCTURAL DETERMINATION OF ADDUCT STEREOSTRUCTURE, AND A STEREOSELECTIVE APPROACH TO TRANS-FUSED OCTALIN SYSTEMS

Authors
HAYNES RK LAM KP WILLIAMS ID YEUNG LL
Citation
Rk. Haynes et al., IONIC DIELS-ALDER REACTIONS OF HEXA-3,5-DIENYL TRIMETHYLSILYL ETHER AND ENONES - X-RAY STRUCTURAL DETERMINATION OF ADDUCT STEREOSTRUCTURE, AND A STEREOSELECTIVE APPROACH TO TRANS-FUSED OCTALIN SYSTEMS, Journal of the Chemical Society, Chemical Communications, (24), 1995, pp. 2479-2480
Citations number
5
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
24
Year of publication
1995
Pages
2479 - 2480
Database
ISI
SICI code
0022-4936(1995):24<2479:IDROHT>2.0.ZU;2-N
Abstract
The trimethylsilyl (TMS) and tert-butyldimethylsilyl (TBDMS) ethers of hexa-3,5-dien-1-ol react with cyclohexenones and an acyclic enone, me thyl vinyl ketone (MVK), in the presence of 5-10 mol% of Me(3)SiOSO(2) CF(3) (TMSOTf) in MeCN to provide trans-fused adducts arising via ioni c (Gassman-type) Diels-Alder reactions; structural confirmation for ad duct stereochemistry for this type of reaction is provided by an X-ray structural determination.