Thiazolidine-2-thione directed diastereoselective addition of chlorotitanium enolates to aldimines

Synthesis

Volumn , Issue 14, 2002, Pages 2075-2083

  Ferstl, Eva M ^a   Venkatesan, Hariharan ^a   Ambhaikar, Narendra B ^a   Snyder, James P ^a   Liotta, Dennis C ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

Aldimines; Diastereoselectivity; Enolates; Thiazolidine 2 thiones; Titanium

Indexed keywords

AROMATIC COMPOUNDS; CONDENSATION; NITROGEN;

THERAPEUTICS;

TITANIUM COMPOUNDS;

CHLOROTITANIUM ALDIMINE; CHLOROTITANIUM ENOLATE; IMINE; ISOCYANATE; N (4 METHOXYPHENYL)BENZALDIMINE; NATURAL PRODUCT; NITROGEN; OXIDE; THIAZOLIDINE 2 THIONE; THIAZOLIDINE DERIVATIVE; TITANIUM DERIVATIVE; TITATNIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; POLYMERIZATION; STEREOCHEMISTRY;

EID: 0036400512     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34375     Document Type: Article

References (41)

1. (a) For a review: Drey, C. N. C. In Chemistry, and Biochemistry of Amino Acids. Peptides and Proteins, Vol. 4; Weinstein, B., Ed.; Marcel Dekker: New York, 1997, 242.
2. (b) Cole, D. C. Tetrahedron 1994, 50, 9517.
3. (a) For a review: Cherry, P. C.; Newall, C. E. In Chemistry and Biology of β-Lactam Antibiotics, Vol. 2; Morin, R. B.; Gorman, M., Eds.; Academic: New York, 1982, 361.
4. (b) For a review:Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M., Eds.; American Chemical Society: Washington D.C., 1995.
5. (a) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley: New York. 1996.
6. (b) Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411.
7. (c) Estermann, H.; Seebach, D. Helv. Chim. Acta 1988, 71, 1824.
8. (d) Ojima, I.; Inaba, S. I. Tetrahedron Lett. 1980, 21, 2077.
9. (e) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
10. (f) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
11. (a) Ojima, I.; Inaba, S. I.; Yoshida, K. Tetrahedron Lett. 1977, 18, 3643.
12. (b) Gennari, C. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 629-660.
13. Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
14. (a) Juaristi, E.; Escalante, J. J. Org. Chem. 1993, 58, 2282.
15. (b) Vaccaro, W. D.; Sher, R.; Davis, H. R. Bioorg. Med. Chem. Lett. 1998, 8, 35.
16. (c) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386.
17. (d) Harwood, L. M.; Currie, G. S.; Drew, M. G. B.; Luke, R. W. A. Chem. Commun. 1996, 1953.
18. (e) Guenoun, F.; Zair, T.; Lamaty, F.; Pierrot, M.; Lazaro, R.; Viallefont, P. Tetrahedron Lett. 1997, 38, 1563.
19. Abrahams, I.; Motevalli, M.; Robinson, A. J.; Wyatt, P. B. Tetrahedron 1994, 50, 12755.
20. Boger, D. L.; Honda, T. Tetrahedron Lett. 1993, 34, 1567.
21. Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883.
22. Yan, T.; Hung, A.; Lee, H.; Chang, C.; Liu, W. J. Org. Chem. 1995, 60, 3301.
23. Yan, T.; Tan, C.; Lee, H.; Lo, H.; Huang, T. J. Am. Chem. Soc. 1993, 115, 2613.
24. Fujita, E.; Nagao, Y. Adv. Heterocycl. Chem. 1989, 45, 1.
25. Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775.
26. During the course of this work Silks and collaborators reported stereoselective Aldol condensations of N-acyl selones, where the syn/anti ratio of the obtained products depends on the nature of the aldehyde employed: Li, Z.; Wu, R.; Michalczyk, R.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
27. 4 and freshly distilled (-)-sparteine. The use of diisopropylethylamine in place of (-)-sparteine resulted in similar selectivities, but with lower chemical yields.
28. Nongkunsarn, P.; Ramsden, C. A. Tetrahedron 1997, 53, 3805.
29. Hsiao, C.; Liu, L.; Miller, M. J. J. Org. Chem. 1987, 52, 2201.
30. Izawa, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1979, 53, 555.
31. Delaunay, D.; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604.
32. 13C chemical shifts with those of 4i, 5i and 6i, respectively.
33. Kametani, T.; Furuyama, H.; Fukuoka, Y.; Takeda, H.; Suzuki, Y.; Honda, T. J. Heterocycl. Chem. 1986, 23, 185.
34. Wong, W. Y.; Wong, W. T. J. Organomet. Chem. 1999, 584, 48.
35. PMP-substituted imines derived from aliphatic aldehydes (enolizable aldehydes) have also been subject to investigation. Good selectivities were obtained with i-Pr and s-Bu, but the major anti-product was formed in poor yield (< 20%). α-Deprotonation and/or imine degradation under the reaction conditions compete unproductively with enolate addition to the CN- double bond.
36. Kanazawa, A. M.; Denis, J. N.; Greene, A. E. J. Org. Chem. 1994, 59, 1238.
37. 1H NMR or HPLC.
38. Alternatively, an open transition state model can also be used to rationalize the observed kinetic product stereochemistry. For examples of this, see: (a) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. (b) Saigo, K.; Osaki M.; Mukaiyama, T. Chem. Lett. 1975, 989. (c) Heathcock, C. H.; Hug, K. T.; Flippin, L. A. Tetrahedron Lett. 1984, 25, 5973.
39. Alternatively, an open transition state model can also be used to rationalize the observed kinetic product stereochemistry. For examples of this, see: (a) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. (b) Saigo, K.; Osaki M.; Mukaiyama, T. Chem. Lett. 1975, 989. (c) Heathcock, C. H.; Hug, K. T.; Flippin, L. A. Tetrahedron Lett. 1984, 25, 5973.
40. Alternatively, an open transition state model can also be used to rationalize the observed kinetic product stereochemistry. For examples of this, see: (a) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. (b) Saigo, K.; Osaki M.; Mukaiyama, T. Chem. Lett. 1975, 989. (c) Heathcock, C. H.; Hug, K. T.; Flippin, L. A. Tetrahedron Lett. 1984, 25, 5973.
41. This hypothesis is supported by molecular mechanics calculations.