CHIRAL N-DIENYL-L-PYROGLUTAMIC ESTERS IN ASYMMETRIC HETERO-DIELS-ALDER REACTIONS WITH ACYLNITROSO DIENOPHILES

Authors
BEHR JB DEFOIN A PIRES J STREITH J MACKO L ZEHNDER M
Citation
Jb. Behr et al., CHIRAL N-DIENYL-L-PYROGLUTAMIC ESTERS IN ASYMMETRIC HETERO-DIELS-ALDER REACTIONS WITH ACYLNITROSO DIENOPHILES, Tetrahedron, 52(9), 1996, pp. 3283-3302
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
9
Year of publication
1996
Pages
3283 - 3302
Database
ISI
SICI code
0040-4020(1996)52:9<3283:CNEIAH>2.0.ZU;2-A
Abstract
Asymmetric Diels-Alder reaction of the N-dienyl-L-pyroglutamic esters 1a-h with acyl nitroso dienophiles 4a-h gave diastereoisomeric adducts 6a-n, 7a-n with 12-90 % de, depending on solvents and temperature. An interpretation was gived. The ''allylic effect'' ((pi C=C-sigmaN-C)M O interactions) was found to be effective to account for the conformat ions of the adducts.