Asymmetric synthesis of 2-exo-aminonorbornane-2-endo-carboxylic acid derivatives
1991; Elsevier BV; Volume: 2; Issue: 6 Linguagem: Inglês
10.1016/s0957-4166(00)82170-9
ISSN1362-511X
AutoresCarlos Cativiela, Pilar López, José A. Mayoral,
Tópico(s)Free Radicals and Antioxidants
ResumoThe 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.
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