Synthesis of optically active arylene bis-alanine derivatives carrying orthogonal protecting groups

Tetrahedron Asymmetry

Volumn 9, Issue 3, 1998, Pages 503-512

  Ritzén, Andreas ^a   Basu, Basudeb ^a   Chattopadhyay, Shital K ^a   Dossa, Fahreen ^a   Frejd, Torbjörn ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

3 PHENYLENE BIS ALANINE DERIVATIVE; 4 PHENYLENE BIS ALANINE DERIVATIVE; ALANINE DERIVATIVE; AMINO ACID DERIVATIVE; BIPHENYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; PRIORITY JOURNAL;

EID: 0032512594     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00014-7     Document Type: Article

References (20)

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12. 12. The absolute configuration is assigned from the known absolute configuration of the Rh catalyst ligand. (R,R)-DIPAMP and (S,S)-Me-DuPHOS give (5) amino acids, whereas (R,R)-Me-DuPHOS gives (R) amino acids, see Refs. 6 and 7.
13. 13. Compounds 1 and 2 were synthesised in three steps from DL-serine, see Refs. 14 and 15.
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16. 16. Schmidt, U.; Greisser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B., Synthesis 1992, 487.
17. 17. For convenience, the notation (±)-X is taken to mean a 1:1:1:1 mixture of the four stereoisomers of X.
18. 18. Carlström, A. S.; Frejd, T., Synthesis 1989, 414.
19. 19. Carlström, A. S.; Frejd, T., J. Org. Chem. 1991, 56, 1289.
20. 20. (±)-17 was available to us from another project (unpublished results). (formula presented)