DIELS-ALDER REACTIONS OF 1-SULFINYLDIENES WITH AN ENDOCYCLIC DOUBLE-BOND - THE UNEXPECTED EVOLUTION OF THE N-METHYLMALEIMIDE ADDUCTS

Authors
CARRENO MC CID MB COLOBERT F RUANO JLG SOLLADIE G
Citation
Mc. Carreno et al., DIELS-ALDER REACTIONS OF 1-SULFINYLDIENES WITH AN ENDOCYCLIC DOUBLE-BOND - THE UNEXPECTED EVOLUTION OF THE N-METHYLMALEIMIDE ADDUCTS, Tetrahedron : asymmetry, 5(8), 1994, pp. 1439-1442
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
8
Year of publication
1994
Pages
1439 - 1442
Database
ISI
SICI code
0957-4166(1994)5:8<1439:DRO1WA>2.0.ZU;2-8
Abstract
R)-(1E,3E)-2-Cyclohexenyl-1-vinyl-p-tolylsulfoxide 1a and (R)-(1E, 3E) -N-methyl-3-[2-(p-tolylsulfinyl) vinyl]-1H-indole Ib reacted with N-me thylmaleimide to give Diels-Alder adducts whose in situ evolution thro ugh a tandem sulfoxide-sulfenate rearrangement/dehydration/[4+2]-cyclo addition sequence afforded the all-cis substituted bicycle [2,2,2] oct ene 7 in a highly stereoselective manner.