Versatile stereocontrol in kinetic resolution of a Diphenylphosphinyl-protected α-amino aldehyde by reaction with chiral phosphonates

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9035-9038

  Kreuder, Reinhard ^a,b   Rein, Tobias ^b   Reiser, Oliver ^c  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; KINETICS; RACEMIC MIXTURE; STEREOCHEMISTRY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030830481     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10428-2     Document Type: Article

References (28)

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3. (c) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755.
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6. Helmchen, G. Nomenclature and Vocabulary of Organic Stereochemistry. In Houben-Weyl: Methods of Organic Chemistry, Vol. E21a; Helmchen, G.; Hoffman, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; pp. 1-74.
7. (a) Rein, T.; Anvelt, J.; Soone, A.; Kreuder, R.; Wulff, C.; Reiser, O. Tetrahedron Lett. 1995, 36, 2303-2306.
8. (b) Rein, T.; Kreuder, R.; von Zezschwitz, P.; Wulff, C.; Reiser, O. Angew. Chem., Int. Ed. Engl. 1995, 34, 1023-1025.
9. (c) Rein, T.; Kann, N.; Kreuder, R.; Gangloff, B.; Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 556-558.
10. (d) Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802-3804.
11. (a) Ramage, R.; Hopton, D.; Parrott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. I 1984, 1357-1370, and references therein.
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13. (c) Andersson, P. G.; Guijarro, D.; Tanner, D. Synlett 1996, 727-728, and references therein.
14. (d) Osborn, H. M. I.; Cantrill, A. A.; Sweeney, J. B.; Howson, W. Tetrahedron Lett. 1994, 35, 3159-3162, and references therein.
15. 3 50:50:1 as eluent) to give geometrically pure compounds (see example below). Diastereomer ratios for each alkene isomer were unchanged after chromatography. ™;Mo, R-1)HC|M)TOC J CO2R-J StChromWoflraph, ( J0 3 (S,Z;.-(H,.2>-99:1 4 (H EWSE)=SB: 12 S (S,Z):(R,Z)-99:\ 3:4*68:32 56% yield
16. 8a in analogy with the method used for 2a-d.
17. 3b Assignments of absolute configurations for 3b and 4b follow by analogy.
18. (a) Ando, K. J. Org. Chem. 1997, 62, 1934-1939.
19. (b) Ando, K. Tetrahedron Lett. 1995, 36, 4105-4108.
20. (c) Kokin, K.; Motoyoshiya, J.; Hayashi, S.; Aoyama, H. Synth. Commun. 1997, 27, 2387-2392.
21. In entry 12, both alkene isomers were obtained predominantly with (S)-configuration at the allylic stereocenter. This fact indicates that the mechanistic details (eg., rate-determining step of the reaction) might differ between reactions using Li bases on the one hand and K or Na bases on the other.
22. For another example of the preparation of (E)-alkenes from a bis(trifluoroethyl) phosphonate, see: Sano, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. Chem. Commun. 1997, 559-560.
23. For reviews, see: (a) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475-1490.
24. (b) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56.
25. Our mechanistic model is based on the assumption that the initial addition of the phosphonate enolate to the aldehyde is irreversible. This assumption is likely to be correct for reagents containing a relatively electron-deficient phosphoryl unit (eg., 2a and 2e), at least in the absence of strongly coordinating counterions such as Li; for other reagents, however, the reaction mechanism might well depend on the specific conditions. For an excellent review which includes mechanistic discussions, see: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
26. For a review, see: Gung, B. W. Tetrahedron 1996, 52, 5263-5301.
27. For a review, see: Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468.
28. For a postulated similar effect, see reference 4c.