References
- Kleinert , H. D. 1967 . Am. J. Hypertens. , 2 : 800 b) J. R. Luly, N. Ba Maung, J. L. Soderquist, A. K. L. Fung, H. D. Stein, H. D. Klienert, P. A. Marcotte, D. A. Egan, B. Bopp, I. Merits, G. Bolis, J. Greer, T. J. Perun and J. J. Plattner, J. Med. Chem., 31, 2264(1988); c) J. R. Luly, C.-N. Hsiao, N. Ba Maung and J. J. Plattner, J. Org. Chem., 53, 6109(1988); d) R. A. Rivero and W. J. Greenlee, Tetrahedron Lett., 32, 2453(1992).
- It has been our experience that many methods are effective for the small scale production of α- amino-aldehydes of high enantiopurity, scale-up of these procedures, however, typically provided material of greatly reduced enantiopurity due to the various technical problems discussed in the following text
- Jurczak , J. and Golebiowski , A. 1989 . Chem. Rev. , 89 : 149 b) For previous reports on the synthesis of 1 see reference 1c and J. R. Luly, J. F. Dellaria, J. J. Plattner, J. L. Soderquist and Y. Yi, J. Org. Chem., 52, 1487(1987); c) M. R. Leanna, H. E. Morton and T. J. Sowin, Tetrahedron Lett., 32, 5029(1992).
- Manusco , A. J. and Swern , D. 1981 . Synthesis , : 165 b) T. T. Tidwell, Org. React., 39, 297(1990).
- See reference 1c for original synthesis of 4
- DeCamp , A. E. , Kawaguchi , A. T. , Volante , R. P. and Shinkai , I. 1991 . Tetrahedron Lett. , 32 : 1867 Similar findings were recently reported: The racemization problem encountered by these workers was solved by a low temperature quench of the reaction mixture with acetic acid.
- Denis , J. N. , Correa , A. and Greene , A. E. 1991 . J. Org. Chem. , 56 : 6939 Hunig's base has been used in the Moffat Swern oxidation of (S)-phenylglycinol to its corresponding, configurationably labile, α-amino-aldehyde: and references therein.
- Parikh , J. R. and von Doering , W. E. 1967 . J. Am. Chem. Soc. , 89 : 5505 b) Y. Hamada and T. Shioiri, Chem. Pharm. Bull. Jpn, 30, 1921(1982).
- This is undoubtedly due to the generation of the corresponding sulfur ylide during the pre-reaction mixing of pyridine-sulfur trioxide complex with triethylamine (see ref. 4 for a discussion of the side reactions of this process)