Chiral N-dienyl-L-pyroglutamic esters in asymmetric hetero-Diels-Alder reactions with acylnitroso dienophiles

DOI: 10.1016/0040-4020(95)01111-0

Source and publish data:

Tetrahedron p. 3283 - 3302 (1996)

Update date:2022-08-04

Topics:

Authors:

Behr, Jean-Bernard

Defoin, Albert

Pires, Joaquim

Streith, Jacques

Macko, Ludwig

Zehnder, Margaretha

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Article abstract of DOI:10.1016/0040-4020(95)01111-0

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 given. The 'allylic effect' (π(C=C) - σ*(N-C) MO interactions) was found to be effective to account for the conformations of the adducts.

Full text of DOI:10.1016/0040-4020(95)01111-0

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