Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts

Journal of the American Chemical Society

Volumn 120, Issue 18, 1998, Pages 4548-4549

  Ferraris, Dana ^a   Young, Brandon ^a   Dudding, Travis ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001209391     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9802450     Document Type: Letter

References (42)

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13. and the nikkomycins and the neopolyoxins (Helms, G. L.; Moore, R. E.; Niemczura, W. P.; Patterson, G. M. L.; Tomer, K. B.; Gross, M. L. J. Org. Chem. 1988, 53, 1298).
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28. Analysis of compound 3a (see Supporting Information) establishes the sense of induction as S by comparison with a product derived from natural aspartic acid, see: Wessig, P.; Steiner, A.; Posborn, K. HelV. Chim. Acta 1996, 79, 1843. Stereoregularity is inferred over the range of products.
29. Enantiomeric excesses (ee's) were measured by HPLC employing a Chiralcel OD column, with EtOH/hexane as eluent.
30. 4, see: Kubas, G. J. Inorganic Synthesis; Shriver, D. F., Ed.; Plenum: New York, 1979; Vol. XIX, p 90.
31. After our initial submission a Cu(II) phosphine complex was used as an asymmetric catalyst, see: Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
32. Chiral Cu(I)-based bisimine and bisoxazoline complexes are effective catalysts for asymmetric cyclopropanation and aziridination reactions, see, for cyclopropanation: (a) Doyle, M. P. Recl. Trav. Chim. Pays-Bas 1991, 110, 305.
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36. For aziridination: (e) Li, Z.; Conser, R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
37. (f) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
38. Product formation was measured by analysis of quenched aliquots of reaction mixtures by HPLC.
39. Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649.
40. 3 produces little shift in the carbonyl band; also see ref 10.
41. MO calculations were performed using the Spartan program (version 5.0.3).
42. Cotton, F. A.; Wilkinson, G. AdVanced Inorganic Chemistry; Wiley-Interscience: New York, 1988; p 756.