Proline-Catalyzed Imino-Diels-Alder Reactions: Synthesis of meso-2,6-Diaryl-4-piperidones

Amine‐catalyzed imino‐Diels–Alder reactions of acyclic α,β‐unsaturated ketones with imines have been developed. L‐Proline catalyzed the in situ generation of 2‐amino‐1,3‐butadienes to provide a stereoselective synthesis of meso‐2,6‐diaryl‐4‐piperidones in one direct step.

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2006-11, Vol.348 (16-17), p.2443-2448
Main Authors: Aznar, Fernando, García, Ana-Belén, Cabal, María-Paz
Format: Article
Language:English
Subjects:
2-amino-1
2‐amino‐1,3‐butadienes
3-butadienes
6-diaryl-4-piperidones
hetero-Diels-Alder reaction
L-proline
meso-2
meso‐2,6‐diaryl‐4‐piperidones
nitrogen heterocycles
organic catalysis
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Description
Summary:Amine‐catalyzed imino‐Diels–Alder reactions of acyclic α,β‐unsaturated ketones with imines have been developed. L‐Proline catalyzed the in situ generation of 2‐amino‐1,3‐butadienes to provide a stereoselective synthesis of meso‐2,6‐diaryl‐4‐piperidones in one direct step.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200600318