STEREOSELECTIVITY IN THE HOMO-DIELS-ALDER REACTION - EFFECT OF A REMOTE 7-SUBSTITUENT ON NICKEL-CATALYZED CYCLOADDITIONS

Authors
LAUTENS M TAM W EDWARDS LG
Citation
M. Lautens et al., STEREOSELECTIVITY IN THE HOMO-DIELS-ALDER REACTION - EFFECT OF A REMOTE 7-SUBSTITUENT ON NICKEL-CATALYZED CYCLOADDITIONS, Journal of the Chemical Society. Perkin transactions. I, (15), 1994, pp. 2143-2150
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
15
Year of publication
1994
Pages
2143 - 2150
Database
ISI
SICI code
0300-922X(1994):15<2143:SITHR->2.0.ZU;2-9
Abstract
7-Substituted norbornadienes have been shown to undergo highly stereos elective homo-Diels-Alder reactions with a variety of dienophiles. Exc ellent exo/endo selectivity (always >97:3) was observed when methyl vi nyl ketone was used as dienophile. Increasing anti/syn selectivity (up to 95:5 when Y = OBu(t)) was observed as the electronegativity of the 7-substituent increased.