139237-38-0Relevant academic research and scientific papers
ASYMMETRIC SYNTHESIS OF 2-EXO-AMINONORBORNANE-2-ENDO-CARBOXYLIC ACID DERIVATIVES
Cativiela, Carlos,Lopez, Pilar,Mayoral, Jose A.
, p. 449 - 456 (2007/10/02)
The Diels-Alder reaction of cyclopentadiene with N-acetyl-α,β-didehydroalaninate of (-)-cis-3-hydroxy isobornyl neopentyl ether yields the corresponding 2-endo(exo)-acetamido-5-norbornene-2-exo(endo)-carboxylates with total diastereofacial selectivity and with a preference for the cycloadduct with the ester group placed at the endo position.So this dienophile is complementary with the previously described (-)-menthyl N-acetyl-α,β-didehydroalaninate for the asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids, since with the latter dienophile exo cycloadducts are preferably obtained with a high diastereofacial selectivity.
Diels-Alder reactions of methyl-N-acyl-α,β-dehydroalaninates with cyclopentadiene
Bueno, M. P.,Cativiela, C.,Finol, C.,Mayoral, J. A.,Jaime, C.
, p. 2182 - 2186 (2007/10/02)
A study has been made of the Diels-Alder reaction of methyl-N-acetyl (and benzoyl)-α,β-dehydroalaninates with cyclopentadiene.In the reaction of methyl-N-acetyl-α,β-dehydroalaninate total conversion is obtained under several conditions, while the N-benzoy
