Asymmetric Wolff rearrangement reactions with α-alkylated-α-diazoketones: Stereoselective synthesis of α-substituted-β-amino acid derivatives

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2177-2179

  Yang, Hua ^a   Foster, Katherine ^a   Stephenson, Corey R J ^a   Brown, William ^a   Roberts, Edward ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001245296     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006146k     Document Type: Article

References (26)

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3. (c) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
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7. a) Asymmetric Synthesis; Morrison, D. D., Ed.; Academic Press: Orlando, FL, 1983-1986; Vols. 1-5.
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10. For details, see the Supporting Information.
11. Kaplan, F.; Meloy, G. K. J. Am. Chem. Soc. 1966, 88, 950.
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14. (c) Tomioka, H.; Okuno, H.; Izawa, Y. J. Org. Chem. 1980, 45, 5278.
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18. For some recent discussions about the regioselectivity of additions to ketenes, see: (a) Sung, K.; Tidwell, T. T. J. Am. Chem. Soc. 1998, 120, 3043.
19. (b) Allen, A. D.; Tidwell, T. J. Org. Chem. 1999, 64, 266.
20. 6 suggest that the most likely lowest energy conformation of the anti product is the one as shown in Scheme 4.
21. Molecular modeling studies of the ketene hemiacetal and the anti and syn products suggest that the most likely transition state may be the one resembling the lowest energy conformation of the final product, as shown in Scheme 4, i.e., a later-transition state. The molecular modeling studies were performed using a Sybyl software package, version 6.0, with a SiliconGraphics workstation.
22. For trapping of ketenes generated from acid chlorides, with chiral alcohols to control the stereochemistry, see: Larsen, R. D.; Corley, E. G.; Davis, P.; Reider, P. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1989, 111, 7650.
23. For recent reviews on synthesis of β-amino acids, see: (a) Cole, D. Tetrahedron 1994, 50, 9517.
24. (b) Enders, D.; Beltray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322.
25. For a stereoselective synthesis of α-alkylated-β-amino acid derivatives using anionic chemistry, see: Podlech, J.; Seebach, D. Liebigs Ann. 1995, 1217, and references therein. For a stereoselective synthesis of α-alkylated-β-amino acid derivatives using free radical chemistry, see: Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507, and references therein.
26. For a stereoselective synthesis of α-alkylated-β-amino acid derivatives using anionic chemistry, see: Podlech, J.; Seebach, D. Liebigs Ann. 1995, 1217, and references therein. For a stereoselective synthesis of α-alkylated-β-amino acid derivatives using free radical chemistry, see: Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507, and references therein.