Asymmetric Diels-Alder Reaction of Aminodienes with a Nonracemic Acrylate Bound to Rink Resin: A Comparison of These Reactions with Their Solution-State Analogues

The asymmetric Diels–Alder reactions between (3R)‐4,4‐dimethyl‐2‐oxopyrrolidin‐3‐yl acrylate derivatives and three N‐Z‐protected 1‐aminodienes have been investigated both in solution and on a solid support. Comparable results for each reaction were observed with the formation of the corresponding co...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2008-01, Vol.2008 (2), p.308-318
Main Authors: Songis, Olivier, Géant, Pierre Yves, Sautrey, Guillaume, Martinez, Jean, Calmès, Monique
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Chiral auxiliaries
Cyclic β-amino acids
Diels-Alder reactions
Microwave activation
Supported synthesis
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Summary:The asymmetric Diels–Alder reactions between (3R)‐4,4‐dimethyl‐2‐oxopyrrolidin‐3‐yl acrylate derivatives and three N‐Z‐protected 1‐aminodienes have been investigated both in solution and on a solid support. Comparable results for each reaction were observed with the formation of the corresponding constrained cyclic β‐amino acids in high yield and moderate‐to‐good selectivity when using optimized conditions. A detailed comparison of both solution and solid‐support synthesis by conventional heating and microwave activation revealed that the microwave technique is often advantageous. We have also demonstrated that reaction on a solid support offered an excellent resolution of the problem of low reactivity and instability of the reagents.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700677