A useful route to (R)- and (S)-tert-leucine

Chirality

Volumn 13, Issue 1, 2001, Pages 43-47

  Allenmark, Stig ^a   Lamm, Bo ^b  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

2 furyllithium; Enantiomers; Imine reduction; Resolution; Tert butyl cyanide; Tert leucine

Indexed keywords

1 (2 FURYL) 2,3 DIMETHYLPROPYLAMINE; AMINE; AMINO ACID DERIVATIVE; TERT LEUCINE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; ENANTIOMER; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0035191195     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/1520-636X(2001)13:1<43::AID-CHIR9>3.0.CO;2-G     Document Type: Article

References (14)

1. Hlavacek J, Marcova R, Jezek R, Slaninova J. Utilization of some non coded amino acids as isosters of peptide building blocks. Amino Acids 1996;11:367-477.
2. Gershonov E, Granoth R, Tzehoval E, Gaoni Y, Fridkin M. 1-Amino-cyclobutane-carboxylic acid derivatives as novel structural elements in bioactive peptides: application to tuftsin analogs. J Med Chem 1996; 39:4833-4843.
3. Bommarius AS, Schwarm M, Stingl K, Kottenhahn M, Huthmacher K, Drauz K. Synthesis and use of enantiomerically pure tert-leucine. Tetrahedron: Asymmetry 1995;6:2851-2888.
4. Adger B, Dyer U, Lennon I, Tiffin P, Ward S. A novel synthesis of tert-leucine via a Leuckart type reaction. Tetrahedron Lett 1997;38: 2153-2154.
5. Demir A. A novel synthesis of optically active α-amino acids. Pure Appl Chem 1997:69:105-108.
6. Pospísek J, Blaha K. tert-Leucine and its simple peptides. Collect Czech Chem Commun 1977;42:1069-1076.
7. 5]enkephalin amide. Helv Chim Acta 1980:63:824-831.
8. Greenstein JP, Winitz M. Chemistry of the amino acids. New York: John Wiley, 1961. p 2583.
9. Pirkle WH, Finn JM. Chiral high-pressure liquid chromatographic stationary phases. 3. General resolution of arylalkylcarbinols. J Org Chem 1981:46:2935-2938.
10. Pirkle WH. Personal communication.
11. Carlsen PHJ, Katsuki T, Martin VS, Sharpless KB. Improved procedure for ruthenium tetraoxide catalyzed oxidations of organic compounds. J Org Chem 1981:46:3936-3938.
12. Nuñez MT, Martín VS. Efficient oxidation of phenyl groups to carboxylic acids with ruthenium tetraoxide. J Org Chem 1990:55:1928-1932.
13. Herriot A, Picker D. Purple benzene: permanganate oxidations using quaternary ammonium ions. Tetrahedron Lett 1974:1511-1514.
14. Krapcho A, Larson J, Eldridge J. Potassium permanganate oxidations of terminal olefins and acetylenes to carboxylic acids of one less carbon. J Org Chem 1977;42:3749-3753.