131102-01-7Relevant articles and documents
The use of heterogeneous catalysis in Diels-Alder reactions of N-acetyl-α,β-dehydroalaninates
Cativiela,Cativiela, Carlos,Garcia,Garcia, Josel,Mayoral,Mayoral, Jose A.,Pires,Pires, Elisabet,Royo,Royo, Ana J.,Figueras,Figueras, Francois
, p. 1295 - 1300 (1995)
Several solids have been tested as heterogeneous catalysts in the Diels-Alder reactions of the relatively unreactive dienophils methyl (1a) and (-)-menthyl (1b) α,β-dehydroalaninates with cyclopentadiene, which is the key step in the assymmetric synthesis
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.
