Synthesis of Fmoc-/Boc-/Z-β-amino acids via Arndt-Eistert homologation of Fmoc-/Boc-/Z-α-amino acids employing BOP and PyBOP

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 42, Issue 7, 2003, Pages 1691-1695

  Vasanthakumar, G R ^a   Babu, V V Suresh ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1H BENZOTRIAZOL 1 YL N OXYTRIS(DIMETHYLAMINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE; 1H BENZOTRIAZOL 1 YL N OXYTRISPYRROLIDINOPHOSPHONIUM HEXAFLUOROPHOSPHATE; AMINO ACID DERIVATIVE; CRYSTALLIN; FLUOROPHOSPHATE; KETONE DERIVATIVE; PHOSPHONIUM DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROSCOPY;

EID: 0041559895     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Matthews J L. Braun C. Guibourdenche C, Overhand M & Seebach D, Enantioselective synthesis of β-amino acids, edited by E Juaristi (Wiley-VCH. New York), 1996, 187.
2. Ye T & McKervey M A, Chem Rev, 94, 1994, 1091.
3. Cole D C, Tetrahedron, 32, 1994, 9517.
4. Meier H & Zeller K-P, Angew Chem Internat Edit, 14, 1975, 32.
5. Muller A, Vogt C & Sewald N, Synthesis, 1998, 837.
6. Cheng R P, Gellman S H & DeGrado W F, Chem Rev, 101, 2001, 3219.
7. DeGrado W F, Schneider J P & Hamuro Y, J Pept Res, 54, 1999, 206.
8. Seebach D & Mattews J L, Chem Commun, 1997, 2015.
9. Seebach D, Abele S, Schraiber J V, Martinoui B, Nussbaum A K. Schild H, Schulz H, Henuecke H, Woessner R & Bitsch F, Chimia, 52. 1998, 734.
10. Liu D & DeGrado W F, J Am Chem Soc.,123, 2001, 7553.
11. Hamuro Y, Schneider J P & DeGrado W F, J Am Chem Soc, 121, 1999, 92200.
12. Heinsoo A, Raidaru G, Linask K, Jarv J, Zetterstruom M & Langel U, Tetrahedron: Asymmetry, 6, 1995, 2245.
13. Gulchard G, Abele S & Seebach D, Helv Chim Acta, 81, 1998, 187.
14. Ellmerer-Muller E P, Brossner D. Maslouh N & Tako A, Helv Chim Acta, 81, 1998, 59.
15. Vasanthakumar G R & Suresh Babu V V, Synth Commun, 32, 2002, 659.
16. Leggio A, Liguori A, Procopio A & Sindona G, J Chem Soc, Perkin Trans 1, 1997, 1969.
17. Ananda K, Gopi H N & Suresh Babu V V, J Pept Res, 55, 2000, 289.
18. Suresh Babu V V, Gopi H N & Ananda K, J Pept Res, 53, 1999, 308.
19. Vasanthakumar G R, Patil B S & Suresh Babu V V, J Chem Soc, Perkin Trans 1, 2002, 2087.
20. Lloyd-Williams P, Albericio F & Giralt E, Chemical approaches to the synthesis of peptides and proteins. (CRC Press, Boca), 1997, 19.
21. Albericio F, Chinchilla R, Dodsworth D J & Najera C, Org Prep Proc Int. 33, 2001, 203.
22. Castro B & Dormoy J-R, Bull Soc Chim, 1973, 3359.
23. Castro B, Ddormoy J-R, Euin G & Selve Cc, J Chem Res (S), 1977, 182.
24. Coste J, Le-Nguyen D & Castro B, Tetrahedron Lett, 31, 1990, 205.
25. Rabanal F, Haro I, Reig F & Garcia-Anton J M, J Chem Soc. Perkin Trans 1, 1991, 945.
26. Hoeg-Jensen T, Jakobsen M H, Olsen C E & Holm A, Tetrahedron Lett, 32, 1991, 7617.
27. Yamamura N, Yamada S, Kohno K, Okuda N, Araki S, Kobayashi K, Kavakai R, Kano K & Kawai M, J Chem Soc, Perkin Trans 1, 1999, 2943.
28. Zaho X, Metz W A, Sieber F & Janda K D. Tetrahedron Lett, 39, 1998, 8433.
29. Furniss B S, Hannaford A J, Smith P W & Tatchell A R, Vogels textbook of practical organic chemistry, (ELBS, Singapore), 1997, 430.
30. Arndt F, Organic synthesis, Coll. Vol. 2, 1943, 165.