Tetrahedron

New syntheses of α-amino acids based on N-acylimino acetates

T Bretschneider, W Miltz, P Münster, W Steglich

Index: Bretschneider, Thomas; Miltz, Wolfgang; Muenster, Peter; Steglich, Wolfgang Tetrahedron, 1988 , vol. 44, # 17 p. 5403 - 5414

Full Text: HTML

Citation Number: 87

Abstract

The reaction of N-acylamino-2-bromoacetes 2 (via N-acylimino acetates 3) with higher order mixed cuprates, trimethysilyl enol ether and β-dicarbonyl compounds leads to a variety of α- amino acid derivatives. Their conversion into the free amino acids can be conveniently carried out by the use of t-butyl protection. In case of the N-acetyl compounds cleavage of the protecting group and optical resolution can be achieved in one step by hog renal ...

Related Articles:

Highly selective tripeptide thrombin inhibitors

[Journal of Medicinal Chemistry, , vol. 36, # 3 p. 314 - 319]

Structure-based bioisosterism design, synthesis and biological evaluation of novel 1, 2, 4-triazin-6-ylthioacetamides as potent HIV-1 NNRTIs

[Zhan, Peng; Li, Xiao; Li, Zhenyu; Chen, Xuwang; Tian, Ye; Chen, Wenmin; Liu, Xinyong; Pannecouque, Christophe; Clercq, Erik De Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 23 p. 7155 - 7162]

Inhibitors of phenylalanine ammonia-lyase: 1-aminobenzylphosphonic acids substituted in the benzene ring

[Phytochemistry, , vol. 59, # 1 p. 9 - 21]

The synthesis of amino acids by reaction of an electrophilic glycine cation equivalent with carbon nucleophiles

[O'Donnell, Martin J.; Falmagne, Jean-Bernard Tetrahedron Letters, 1985 , vol. 26, # 6 p. 699 - 702]

Reactions of Amines. XV. Synthesis of α-Amino Acids from Imino Esters1, 2

[Journal of Organic Chemistry, , vol. 31, p. 3708 - 3711]

More Articles...