Enantioselective synthesis of. beta.-amino acids. 2. Preparation of the like stereoisomers of 2-methyl-and 2-benzyl-3-aminobutanoic acid

…, J Escalante, B Lamatsch, D Seebach

Index: Juaristi, Eusebio; Escalante, Jaime; Lamatsch, Bernd; Seebach, Dieter Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2396 - 2398

Full Text: HTML

Citation Number: 70

Abstract

An improved procedure for the preparation of (R)-and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the correaponding (1'8-N-phenethyl derivatives 1 is reported. From 2a, the four poasible stereisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3. In the cyclization of 3, the ciaproducts 4 predominate ca. 95: 5. These heterocycles can be alkylated (LDA, RX), as demonstrated ...

Related Articles:

Homochiral lithium amides for the asymmetric synthesis of β-amino acids

[Davies, Stephen G.; Garrido, Narciso M.; Kruchinin, Dennis; Ichihara, Osamu; Kotchie, Luke J.; Price, Paul D.; Mortimer, Anne J. Price; Russell, Angela J.; Smith, Andrew D. Tetrahedron Asymmetry, 2006 , vol. 17, # 12 p. 1793 - 1811]

Efficient EPC synthesis of β??aminobutanoic acid

[Gmeiner, Peter Liebigs Annalen der Chemie, 1991 , # 5 p. 501 - 502]

Parallel synthesis of homochiral β-amino acids

[Davies, Stephen G.; Mulvaney, Andrew W.; Russell, Angela J.; Smith, Andrew D. Tetrahedron Asymmetry, 2007 , vol. 18, # 13 p. 1554 - 1566]

The Enantioselective Synthesis of β??Amino Acids, their α??hydroxy derivatives, and the N??terminal components of bestatin and microginin

[Jefford, Charles W.; McNulty, James; Lu, Zhi-Hui; Wang, Jian Bo Helvetica Chimica Acta, 1996 , vol. 79, # 4 p. 1203 - 1216]

Comparative Theoretical Study of the Ring-Opening Polymerization of Caprolactam vs Caprolactone Using QM/MM Methods

[Li, Xiang-Guo; Laehitie, Maria; Kanerva, Liisa T. Tetrahedron Asymmetry, 2008 , vol. 19, # 15 p. 1857 - 1861]

More Articles...