HIGHLY REGIOSELECTIVE, STEREOSELECTIVE, AND CHEMOSELECTIVE DIELS-ALDER REACTION OF MONOTHIOMALEIMIDE, AN AMBIDENT C=S AND C=C DIENOPHILE

Authors
TAMARU Y SAKATA H KIMURA M HARAYAMA H KONISHI H FUGAMI K TANAKA S
Citation
Y. Tamaru et al., HIGHLY REGIOSELECTIVE, STEREOSELECTIVE, AND CHEMOSELECTIVE DIELS-ALDER REACTION OF MONOTHIOMALEIMIDE, AN AMBIDENT C=S AND C=C DIENOPHILE, Journal of the Chemical Society, Chemical Communications, (20), 1994, pp. 2365-2366
Citations number
26
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
20
Year of publication
1994
Pages
2365 - 2366
Database
ISI
SICI code
0022-4936(1994):20<2365:HRSACD>2.0.ZU;2-P
Abstract
The thiocarbonyl group of monothiomaleimide 1 serves as a more reactiv e dienophile than the electron-deficient C=C double bond in the same m olecule for the Diets-Alder reaction with dienes 2c-g and provides ort ho-endo products 3 exclusively or predominantly over the other possibl e adducts 4-10.