Asymmetric synthesis of β-amino alcohols and 1,2-diamines through DuPHOS-Rh catalysed hydrogenation

Tetrahedron Letters

Volumn 40, Issue 36, 1999, Pages 6685-6688

  Burk, Mark J ^a   Johnson, Nicholas B ^a   Lee, Jeffrey R ^b  

^a Chirotech Technology Ltd   (United Kingdom)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIAMINE DERIVATIVE; ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; HYDROGENATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033520219     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01376-3     Document Type: Article

References (19)

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3. See for example: M.J. McKennon and A.I. Meyers, J. Org. Chem. 1993, 58, 3568 and references therein.
4. P. Newman, Optical Resolution Procedures for Chemical Compounds, Volume 1, Amines and Related Compounds, Optical Resolution Information Center, New York, 1981.
5. M.J. Burk in Chiral Chemicals, D.J. Ager (Ed), Marcel Dekker, New York, 1999, Chapter 18.
6. M.J. Burk, J.G. Allen and W.F. Kiesman, J. Am. Chem. Soc. 1998, 120, 657.
7. M.J. Burk, G. Casy and N.B. Johnson, J. Org. Chem, 1998, 63, 6084.
8. M.J. Burk, F. Bienewald, M. Harris and A. Zanotti-Gerosa, Angew. Chem., Int. Ed. 1998, 37, 1931.
9. G. Zhu, A.L. Casalnuovo and X. Zhang, J. Org. Chem. 1998, 63, 8100.
10. Y. Nakamura and C. Shin, Synthesis, 1993, 1158.
11. U. Schmidt, H. Griesser, V. Leitenberger, A. Lieberknecht, R. Mangold, R. Meyer, B. Riedl, Synthesis 1992, 487.
12. The catalysts used for the study have the general formulae: [(Et-DuPHOS)Rh(COD)]OTf and [(Me- DuPHOS)Rh(COD)]OTf.
13. 2 and stirred at 20-25 °C for 12 h or until no further hydrogen uptake was observed. The reactions were then evaporated and the residue passed through a short silica plug in EtOAc:hexane ( 1:1) to remove catalyst residues. The products obtained were analysed directly, without further purification, for conversion and/or enantiomeric excess.
14. The absolute configuration was assigned either by direct comparison to β-amino alcohols prepared by an alternative route or by reference to literature values for optical rotation.
15. 4) and evaporated. The resultant residue was purified by flash chromatography to afford the dehydro-α-amino aldoximes 8.
16. Due to the geometric isomers of the oxime function, the two diastereomers of the products 9 could not be resolved using our standard GC and HPLC analytical techniques.
17. M.J. Burk, Synlett, Accounts Article, 1999, in preparation.
18. M.T. Reetz, M.W. Drews and A. Schmitz, Angew. Chem., Int. Ed. Engl. 1987, 26, 1141; J. Jurczak and A. Golebiowski, Chem. Rev. 1989, 89, 149.
19. M.T. Reetz, M.W. Drews and A. Schmitz, Angew. Chem., Int. Ed. Engl. 1987, 26, 1141; J. Jurczak and A. Golebiowski, Chem. Rev. 1989, 89, 149.