Synthesis of a β-hexapeptide from (R)-2-aminomethyl-alkanoic acids and structural investigations

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 437-438

  Hintermann, Tobias ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000193384     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6117     Document Type: Article

References (12)

1. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
2. Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Oberer, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996, 79, 2043.
3. For a review see: Matthews, J. L.; Braun, C.; Guibourdenche, C.; Overhand, M.; Seebach, D. Chapter 5 in Enantioselective Synthesis of β-Amino Acids, Juaristi, E., Ed., VCH, Weinheim and New York, 1997.
4. Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, S. C.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
5. For alternative methodologies, see the monograph referred to in (2) and: Juaristi, E.; Quintana, D.; Balderas, M.; Garcia-Pérez, E. Tetrahedron Asymmetry 1996, 7, 2233.
6. We have no indication of racemization en route from the diastereoisomerically pure oxazolidinones to the β-amino acid and β-peptide derivatives described herein. The absolute configuration (R) of 3-5 follows from optical comparison.
7. Talley, J. J. (Monsanto Co., USA), Eur. Pat. Appl. EP 396 526, 1990; Chem. Abstr. 1991, 114, 229382.
8. Houben-Weyl, Synthese von Peptiden, Volume 15, Part 1+2, Wünsch, E., Ed., G. Thieme, Stuttgart, 1974.
9. 3-peptides.
10. We use the "old-fashioned" nomenclature for the absolute configuration in this case, because the (R/S) nomenclature gives opposite configurations for β-HVal versus β-HAla and β-HLeu! This is not the case for the β-amino acid residues in 9.
11. 3-peptides leads to a complete loss of the typical CD pattern.
12. 4 (= 0 ppm), J in Hz; Carbon multiplicities were assigned by DEPT techniques. MS: VG ZAB2-SEQ with 3-nitrobenzyl alcohol (FAB, 3-NOBA).