ALPHA-CYCLIZATION OF TERTIARY-AMINES .3. CAPTODATIVE OR PUSH-PULL ENAMINES FORM PYRROLINES, PYRROLIZIDINES AND THEIR RING HOMOLOGS WITH DIMETHYL ACETYLENEDICARBOXYLATE IN A HIGHLY DIASTEREOSELECTIVE REACTION
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DEBOECK, B
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UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUMUNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUM
DEBOECK, B
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JIANG, SP
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UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUMUNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUM
JIANG, SP
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JANOUSEK, Z
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UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUMUNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUM
JANOUSEK, Z
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VIEHE, HG
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UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUMUNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUM
VIEHE, HG
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[1] UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUM
The title one-pot reaction occurs through a sequence of [2+2] cycloaddition ring opening to dienamines and formation of a 1,5-dipole by [1,6] hydrogen-shift. This intermediate may cyclize or in sterically suitable cases and at lower temperatures, lead to isolable N-vinyl enamines by proton transfer.