131053-13-9Relevant articles and documents
The Diels-Alder reactions of polymer bound dehydroalanine derivatives
Burkett, Brendan A.,Chai, Christina L. L.
, p. 7035 - 7038 (1999)
The synthesis and Diels-Alder cycloadditions of a number of polymer bound dehydroalanine derivatives are described. The studies compare methodologies for accessing polymer bound dehydroalanines and establish the versatility and efficiency of solid phase Diels-Alder reactions in the synthesis of carbocyclic amino acids. These studies nicely complement the growing repertoire of methodologies for the functionalisation of amino acid derivatives.
N-Fmoc-dehydroalanine: A versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids
Burkett,Chai
, p. 6661 - 6664 (2007/10/03)
The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.
ASYMMETRIC SYNTHESIS OF CYCLOALIPHATIC α-AMINO ACIDS WITH A NORBORNANE SKELETON
Cativiela, Carlos,Lopez, Pilar,Mayoral, Jose A.
, p. 379 - 388 (2007/10/02)
The asymmetric synthesis of endo and exo 2-aminonorbornane-2-carboxylic acids is carried out via the Diels-Alder reaction between cyclopentadiene and (-)-menthyl N-acetyl-α,β-dehydroalaninate.It is shown that this dienophile is more reactive than the corresponding methyl ester, which opens the way for the use of chiral N-acetyl-α,β-dehydroalaninates as dienophiles in asymmetric Diels-Alder reactions.As high diastereofacial selectivity is obtained with what was previously considered a mediocre chiral auxiliary, the acetamido group must play an important role, which is discussed.
