Synthesis of C-protected α-amino aldehydes of high enantiomeric excess from highly epimerizable N-protected α-amino aldehydes

Organic Letters

Volumn 2, Issue 21, 2000, Pages 3337-3340

  Myers, Andrew G ^a   Zhong, Boyu ^a   Kung, Daniel W ^a   Movassaghi, Mohammad ^a   Lanman, Brian A ^a   Kwon, Soojin ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY DIFFRACTION;

ALDEHYDES; MOLECULAR STRUCTURE; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 0034687186     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006427s     Document Type: Article

References (19)

1. Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401-8402.
2. For leading references to prior work describing the preparation of acetal-, thioacetal-, and aminal-protected α-amino aldehydes, see: (a) Bringmann, G.; Geisler, J.-P. Synthesis 1989, 608-610.
3. (b) Thiam, M.; Chastrette, F. Tetrahedron Lett. 1990, 31, 1429-1432.
4. (c) Enders, D.; Funk, R.; Klatt, M.; Raabe, G.; Hovestreydt, E. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 418-421.
5. (d) Denmark, S. E.; Nicaise, O. Synlett 1993, 359-361.
6. (e) Muralidharan, K. R.; Mokhallalati, M. K.; Pridgen, L. N. Tetrahedron Lett. 1994, 35, 7489-7492.
7. (f) Alexakis, A.; Lensen, N.; Tranchier, J.-P.; Mangeney, P.; Feneau-Dupont, J.; Declercq, J. P. Synthesis -1995, 1038-1049.
8. Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem. Soc. 2000, 122, 3236-3237.
9. For other approaches to minimize racemization of α-amino aldehydes, see: (a) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 236-239.
10. (b) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
11. Myers, A. G.; Zhong, B.; Movassaghi, M.: Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359-1362.
12. Atherton, E.; Sheppard, R. C. In The Peptides; Undenfriend, S., Meienhofer, J., Eds.; Academic Press: San Diego, 1987; Vol. 9, Chapter 1, pp 16-20.
13. Swern oxidation is complicated by the oxidation of the thioether group, see: Wen, J. J.; Crews, C. M. Tetrahedron: Asymmetry 1998, 9, 1855-1858.
14. 1H coupling constants between the methine hydrogens are not reliable indicators of syn or anti stereochemistry. As noted in the discussion above, the preferred conformations of both diastereomers place the α-CH and the amino nitrile CH bonds antiperiplanar. The corresponding coupling constants are thus quite similar and cannot be used to differentiate the diastereomers.
15. (a) Ogata, Y.; Kawasaki, A. J. Chem. Soc. B 1971, 2, 325-329.
16. (b) Taillades. J.; Commeyras, A. Tetrahedron 1974, 30, 2493-2501.
17. (c) Stout, D. M.; Black, L. A.; Matier, W. L. J. Org. Chem. 1983, 48, 5369-5373.
18. Chakraborty, T. K.; Hussain, K. A.; Reddy, G. V. Tetrahedron 1995, 51, 9179-9190.
19. Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828-10829.