2-Lithio-N-BOC-thiazolidines as chiral acyl anion synthons: Evaluation of facial stereoselectivity in the addition of chiral organolithiums to aldehydes

Tetrahedron Asymmetry

Volumn 11, Issue 10, 2000, Pages 2093-2106

  Gawley, Robert E ^a   Zhang, Qianhui ^a   McPhail, Andrew T ^b  

^a University of Miami   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALPHA HYDROXYALDEHYDE; GLYCOL; ORGANOLITHIUM COMPOUND; PROTON; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; DIASTEREOISOMER; INFRARED SPECTROSCOPY; ISOMER; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034595805     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00154-3     Document Type: Article

References (52)

1. Curtin, D. Y.; Harris, E. E.; Meislich, E. K. J. Am. Chem. Soc. 1952, 74, 2901-2904.
2. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 828-5835.
3. Prelog, V. Helv. Chim. Acta 1953, 36, 308-319.
4. Gawley, R. E. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI: Greenwich, CT, 1998; Vol. 3; pp. 77-111.
5. Gawley, R. E. In Grignard Reagents: New Developments; Richey, H. G., Ed.; Wiley & Sons: New York, 2000; pp. 139-164.
6. Seebach, D. Synthesis 1969, 17-36.
7. Kolb, M. In Encylopedia of Reagents for Organic Synthesis; Paquette, L., Ed. 2-Lithio-1,3-dithiane. Wiley & Sons: Chichester, 1995; Vol. 5; pp. 2983-2989.
8. Ko, K.-Y.; Eliel, E. L. J. Org. Chem. 1986, 51, 5353-5362.
9. He, X.-C.; Eliel, E. L. Tetrahedron 1987, 43, 4979-4987.
10. He, X.-C.; Eliel, E. L. J. Org. Chem. 1990, 55, 2114-2119.
11. Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599-2601.
12. Frye, S. V.; Eliel, E. L. Tetrahedron Lett. 1985, 26, 3907-3910.
13. Kogure, T.; Eliel, E. L. J. Org. Chem. 1984, 49, 576-578.
14. Beak, P.; Lee, W.-K. Tetrahedron Lett. 1989, 30, 1197-1200.
15. Beak, P.; Lee, W. K. J. Org. Chem. 1990, 55, 2578-2580.
16. Abatjoglou, A. G.; Eliel, E. L.; Kuyper, L. F. J. Am. Chem. Soc. 1977, 99, 8262-8269.
17. Meyers, A. I.; Hoeve, W. T. J. Am. Chem. Soc. 1980, 102, 7125-7126.
18. Meyers, A. I.; Edwards, P. D.; Rieker, W. F.; Bailey, T. R. J. Am. Chem. Soc. 1984, 106, 3270-3276.
19. Sanner, M. A. Tetrahedron Lett. 1989, 30, 1909-1912.
20. Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119-5122.
21. Pfammatter, E.; Seebach, D. Liebigs Ann. Chem. 1991, 1323-1336.
22. Bernardi, F.; Csizmadia, I. G.; Mangini, A.; Schlegel, H. B.; Whangbo, M.-H.; Wolfe, S. J. Am. Chem. Soc. 1975, 97, 2209-2218.
23. Lehn, J.-M.; Wipff, G. J. Am. Chem. Soc. 1976, 98, 7498-7505.
24. Epiotis, N. D.; Yates, R. L.; Bernardi, F.; Wolfe, S. J. Am. Chem. Soc. 1976, 98, 5435-5439.
25. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702.
26. Kise, N.; Urai, T.; Yoshida, J. Tetrahedron: Asymmetry 1998, 9, 3125-3128.
27. Colombo, L.; Di Giacomo, M.; Brusotti, G.; Delogu, G. Tetrahedron Lett. 1994, 35, 2063-2066.
28. Colombo, L.; Di Giacomo, M.; Brusotti, G.; Milano, E. Tetrahedron Lett. 1995, 36, 2863-2866.
29. Seebach, D.; Syfrig, M. A. Angew. Chem., Int. Ed. Engl. 1984, 3, 248-249.
30. Seebach, D.; Hansen, J.; Seiler, P.; Gromek, J. M. J. Organomet. Chem. 1985, 285, 1-13.
31. Rein, K. S.; Chen, Z.-H.; Perumal, P. T.; Echegoyen, L.; Gawley, R. E. Tetrahedron Lett. 1991, 32, 1941-1944.
32. Rein, K. S.; Gawley, R. E. Tetrahedron Lett. 1990, 31, 3711-3714.
33. Rein, K. S.; Gawley, R. E. J. Org. Chem. 1991, 56, 1564-1569.
34. Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945-2948.
35. Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103-8112.
36. Eliel, E. L. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1983; Vol. 2; pp. 125-155.
37. Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Org. Synth. 1990, Coll. Vol. VII, 530-533.
38. Handrick, G. R.; Atkinson, E. R.; Granchelli, F. E.; Bruni, R. J. Med. Chem. 1965, 8, 762-766.
39. Kurth, M. J.; Tahir, S. H.; Olmstead, M. M. J. Org. Chem. 1990, 55, 2286-2288.
40. Gassman, P. G.; Hodgson, P. K. G.; Balchunis, R. J. J. Am. Chem. Soc. 1976, 98, 1275-1276.
41. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553-3560.
42. Guette, J.-P.; Spassky, N. Bull. Soc. Chim. Fr. 1972, 4217-4224.
43. Ko, K.-K.; Frazee, W. J.; Eliel, E. L. Tetrahedron 1984, 40, 1333-1343.
44. Hoppe, D.; Carstens, A.; Krämer, T. Angew. Chem., Int. Ed. Engl. 1990, 29, 1424-1425.
45. Carstens, A.; Hoppe, D. Tetrahedron 1994, 50, 6097-6108.
46. Faibish, N. C.; Park, Y. S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1997, 119, 11561-11570.
47. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708-9710.
48. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231-3239.
49. Bertini Gross, K. M.; Jun, Y. M.; Beak, P. J. Org. Chem. 1997, 62, 7679-7689.
50. Gawley, R. E. Tetrahedron Lett. 1999, 40, 4297-4300.
51. Kaufmann, E.; Schleyer, P. v. R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560-5562.
52. Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016-11017.