Tetrahedron Asymmetry p. 449 - 456 (1991)
Update date:2022-08-04
Topics:
Cativiela, Carlos
Lopez, Pilar
Mayoral, Jose A.
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.
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Doi:10.1016/S0040-4039(00)79400-7
(1991)Doi:10.1071/CH10464
(2011)Doi:10.1021/jacs.9b06668
(2019)Doi:10.1016/j.tetlet.2012.01.032
(2012)Doi:10.1039/b003793l
(2000)Doi:10.1021/jo00025a025
(1991)