Origin of stereochemistry in the α-amino acid esters and amides generated from optically active zirconaaziridine complexes

Journal of the American Chemical Society

Volumn 118, Issue 14, 1996, Pages 3479-3489

  Gately, Daniel A ^a   Norton, Jack R ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029966522     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953893h     Document Type: Article

References (28)

1. Williams has said that "asymmetric carboxylation [at the α position of an amine] is a surprisingly rarely studied approach [and] .. a future area of investigation". Williams, R M. Synthesis of Optically Active α-Amino Acids, Pergamon: Oxford, 1989, Vol. 7.
2. (a) Meyers, A. I.; Hellring, S ; Hoeve, W. T. Tetrahedron Lett. 1981, 22, 5115.
3. (b) Bolster, J. M.; Hoeve, W T.; Vaalburg, W.; Van Dijk, T. H.; Zijlstra, J. B.; Paans, A. M. J., Wynberg, H., Woldring, M. G Int J. Appl. Radiat Isot. 1985, 36, 339.
4. Duhamel, L , Duhamel, P., Fouquay, S., Eddine, J. J.; Peschard, O.; Plaquevent, J.-C.; Ravard, A , Solliard, R., Valnot, J.-Y ; Vincens, H. Tetrahedron 1988, 44, 5495.
5. Beak, P.; Kerrick, S. T., Wu, S.; Chu, J J. Am Chem. Soc 1994, 116, 3231.
6. Chong, J. M , Park, S. B. J Org. Chem 1992, 57, 2220
7. Buchwald, S L., Watson, B. T., Wannamaker, M. W.; Dewan, J. C. J. Am. Chem Soc 1989, 111, 4486.
8. X-ray analysis of 13b (R = Ph, R′ = o-anisyl) shows the oxygen of the o-anisyl substituent bound to Zr Gately, D A , Norton, J R.; Goodson, P A Unpublished results.
9. Gately, D. A.; Norton, J R.; Goodson, P. A. J. Am. Chem. Soc. 1995, 117, 986.
10. (a) Grossman, R B.; Davis, W. M., Buchwald, S L. J. Am Chem. Soc. 1991, 113, 2321.
11. (b) Grossman, R. B. Ph.D. Thesis, Massachusetts Institute of Technology, Cambridge, MA, 1991.
12. Wild, F R. W P ; Wasiucionek, M ; Huttner, G.; Brintzinger, H. H J Organomet Chem 1985, 288, 63
13. When they attempted to prepare the EBTHI analog of 13a in benzene. Grossman and Buchwald obtained the zirconaisoindole A below Analogous species were formed in all cases when R = aryl and no coordinating atoms were present (see ref 10b). (Equation Presented)
14. 2 was added.
15. Christoskova, St., Berova, B., Simova, E.; Spassov, St., Kurtev, B., Snatzke, G Proceedings of the F.E.C.S. International Conference on Circular Dichroism; VCH: Weinheim, 1987; pp 315-21.
16. Paradisi, M. P., Romeo, A. J. Chem Soc., Perkin Trans. 1 1977, 596.
17. C-H epimerization of the esters 16 (or amides) was not detected (via loss of optical rotation) under the conditions used in the workup procedure.
18. The only exception was the ee (18%) of (S)-32a (R = Rprime; = Ph) Howeser, Grossman reported that the de of its precursor (S,S,S)-41a) varied "with the temperature and other conditions" (refs 10b and 12)
19. (a) Seeman, J. I. Chem. Rev. 1983, 83, 83.
20. (b) Eliel, E L.; Wilen, S. H. Stereochemistry of Organic Compounds: John Wiley and Sons, New York, 1994, pp 648-655.
21. (c) Carey, F. A.; Sundberg, R J Advanced Organic Chemistry, 3rd ed : Plenum, New York, 1990, pp 215-216
22. Low concentrations of isocyanates must be used to effect a significant change in the ee's of the phenyl-substituted amides 19 and 20: the isocyanate must be added as a dilute solution so that mixing is complete before the insertion reaction occurs In contrast, because the o-anisyl-substituted zirconaaziridines react more slowly, the concentrations of isocyanate low, enough to effect a change in the ee's of the o-anisyl-substituted amides 23 and 24 can be added neat to 25b.
23. Grossman suggested that the 30 ⇌ 25 epimerization involved the 43 ⇌ 43′ equilibrium in Scheme 13 (see ref 10b).
24. 6 Moreover, (o-anisyl)N=CH(Ph) did not displace the imine fragment in 45 to give the known complex 13b.
25. (a) Samuel, E., Rausch, M. D. J. Am. Chem. Soc. 1973, 95, 6263
26. (b) References 7 and 9
27. Waymouth, R. M.; Bangerter, F.; Pino, P Inorg. Chem. 1988, 27, 758.
28. Brown, H. C., Choi, Y. M.; Narasmihan, S. J. Org. Chem. 1982, 47, 3153