EPC-synthesis of β-amino acid derivatives through lithiated hydropyrimidines

European Journal of Organic Chemistry

Volumn , Issue 1, 1999, Pages 335-360

  Seebach, Dieter ^a   Boog, Alois ^a   Schweizer, W Bernd ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

2 tert Butylhydropyrimidinones; 3 Aminocarboxylic acid derivatives; Alkylations; Asymmetric synthesis; Cyclic imino esters; Kinetic resolution; Lithium enaminates; Amino acids

Indexed keywords

AMINO ACID DERIVATIVE; BETA AMINO ACID; PYRIMIDINE DERIVATIVE;

ALKYLATION; ARTICLE; DECOMPOSITION; DIASTEREOISOMER; ELECTRON TRANSPORT; ENANTIOMER; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RACEMIC MIXTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032811713     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199901)1999:1<335::AID-EJOC335>3.0.CO;2-A     Document Type: Article

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21. This is also true for doubly lithiated N-acyl 3-aminocarboxylic acid esters which we have shown to react in the 2-position highly selectively with alkyl halides, but not with aldehydes and imines: D. Seebach, H. Estermann, Tetrahedron Lett. 1987, 28, 3103-3106. - H. Estermann, D. Seebach, Helv. Chim. Acta 1988, 71, 1824-1839.
22. This is also true for doubly lithiated N-acyl 3-aminocarboxylic acid esters which we have shown to react in the 2-position highly selectively with alkyl halides, but not with aldehydes and imines: D. Seebach, H. Estermann, Tetrahedron Lett. 1987, 28, 3103-3106. - H. Estermann, D. Seebach, Helv. Chim. Acta 1988, 71, 1824-1839.
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26. 3-Aminopropionic acid was purchased from Senn Chemicals AG Dielsdorf, Switzerland.
27. This β-amino acid was synthesized by Arndt-Eistert homologation from L-alanine; see J. Podlech, D. Seebach, Liebigs Ann. Chem. 1995, 1217-1228.
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34. 4 the corresponding 4-ethoxy analog of 8a was formed but not further studied in deprotonations. The compound is characterized in the experimental section.
35. For unknown reasons the lithiation of the trans isomer 8b failed completely!
36. Double alkylations leading to the analogs of 20 with 5-methyl-5-propargyl and the epimer of 20, were also carried out, but the products (conversion ca. 50 and 80%) could not be separated from starting material. For Li enaminate formation, tBuLi had to be used; therefore reactions with Alloc-and Z-protected analogs were impossible, i.e. not compatible with the allyl and benzyl groups!
37. This analysis was complicated by the presence of rotamers, so that NMR spectra with single sharp signals could only be obtained at high temperature (ca. 90°C for Z-protected derivatives), the Boc-protected products showed two rotamers with sharp signals at room temperature and coalescence behavior at ca. 90°C.
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