Catalytic asymmetric synthesis of new halogenated chiral synthons

Chemistry - A European Journal

Volumn 3, Issue 4, 1997, Pages 517-522

  Vanhessche, Koen P M ^a   Sharpless, K Barry ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b Firmenich Inc   (United States)

Author keywords

asymmetric catalysis; chiral synthons; cyclic sulfates; dihydroxylations; organofluorine compounds

Indexed keywords

EID: 0030900381     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030406     Document Type: Article

References (66)

1. H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483.
2. a) For a review, see: R. M. Hanson, Chem. Rev. 1991, 91, 437;
3. b) J. Jurczak, S. Pikul, T. Bauer, Tetrahedron 1986, 42, 447.
4. For reviews, see: a) G. Resnati, Tetrahedron 1993, 49, 9385; b) J. T. Welch, ibid. 1987, 43, 3123.
5. For reviews, see: a) G. Resnati, Tetrahedron 1993, 49, 9385; b) J. T. Welch, ibid. 1987, 43, 3123.
6. M. Koden, M. Shiomi, K. Nakagawa, F. Funada, K. Awane, T. Yamazaki, T. Kitazume, Jpn. J. Appl. Phys. 1991, 30, L 1300.
7. H. C. Kolb, Y. L. Bennani, K. B. Sharpless, Tetrahedron Asymmetry 1993, 4, 133.
8. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440.
9. G. A. Crispino, K.-S. Jeong, H. C. Kolb, Z.-M. Wang, D. Xu, K. B. Sharpless, J. Org. Chem. 1993, 58, 3785.
10. K. Naemura, T. Mizo-oku, K. Kamada, K. Hirose, Y. Tobe, M. Sawada, Y. Takai, Tetrahedron Asymmetry 1994, 5, 1549.
11. Dihydroxylation (racemic) of trifluoropropene was reported previously: a) W. A. Herrmann, S. J. Eder, W. Scherer, Angew. Chem. 1992, 104, 1371; Angew. Chem. Int. Ed. Engl. 1992, 31, 1345; b) W. A. Herrmann, S. J. Eder, Chem. Ber. 1993, 126, 31.
12. Dihydroxylation (racemic) of trifluoropropene was reported previously: a) W. A. Herrmann, S. J. Eder, W. Scherer, Angew. Chem. 1992, 104, 1371; Angew. Chem. Int. Ed. Engl. 1992, 31, 1345; b) W. A. Herrmann, S. J. Eder, Chem. Ber. 1993, 126, 31.
13. Dihydroxylation (racemic) of trifluoropropene was reported previously: a) W. A. Herrmann, S. J. Eder, W. Scherer, Angew. Chem. 1992, 104, 1371; Angew. Chem. Int. Ed. Engl. 1992, 31, 1345; b) W. A. Herrmann, S. J. Eder, Chem. Ber. 1993, 126, 31.
14. 2AQN (AQN = anthraquinone) ligand, 1b and 1c are dihydroxylated in 81 and 77% ee, respectively, see: H. Becker, K. B. Sharpless, Angew. Chem. 1996, 108, 447; Angew. Chem. Int. Ed. Engl. 1996, 35, 448.
15. 2AQN (AQN = anthraquinone) ligand, 1b and 1c are dihydroxylated in 81 and 77% ee, respectively, see: H. Becker, K. B. Sharpless, Angew. Chem. 1996, 108, 447; Angew. Chem. Int. Ed. Engl. 1996, 35, 448.
16. Asymmetric dihydroxylation of trimethylvinylsilane was reported earlier: a) J. A. Soderquist, A. M. Rane, C. J. Lopez, Tetrahedron Lett. 1993, 34, 1893; b) A. R. Bassindale, P. G. Taylor, Y. Xu, J. Chem. Soc. Perkin Trans. 1 1994, 1061.
17. Asymmetric dihydroxylation of trimethylvinylsilane was reported earlier: a) J. A. Soderquist, A. M. Rane, C. J. Lopez, Tetrahedron Lett. 1993, 34, 1893; b) A. R. Bassindale, P. G. Taylor, Y. Xu, J. Chem. Soc. Perkin Trans. 1 1994, 1061.
18. H. C. Kolb, P. G. Andersson, K. B. Sharpless, J. Am. Chem. Soc. 1994, 116, 1278.
19. a) For syntheses of enantiopure methyloxirane, see M. K. Ellis, B. T. Golding, Org. Synth. 1985, 63, 140;
20. b) S. J. Kuhn, US Patent 3673 264, 1972 (Chem. Abstr. 1972, 77, 139786);
21. c) M. D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 1978, 100, 5491.
22. P. Huszthy, J. S. Bradshaw, C. Y. Zhu, R. M. Izatt, S. Lifson, J. Org. Chem. 1991, 56, 3330.
23. 3,3,3-Trifluoro-1,2-propanediol was previously obtained by hydrolysis of (trifluoromethyl)oxirane, see a) E. T. McBee, T. M. Burton, J. Am. Chem. Soc. 1952, 74, 3022. Enantiopure 2b is a key intermediate in the enantioselective synthesis of trifluorolactic acid, see: b) T. Katagiri, F. Obara, S. Toda, K. Furuhashi, Synlett 1994, 507.
24. 3,3,3-Trifluoro-1,2-propanediol was previously obtained by hydrolysis of (trifluoromethyl)oxirane, see a) E. T. McBee, T. M. Burton, J. Am. Chem. Soc. 1952, 74, 3022. Enantiopure 2b is a key intermediate in the enantioselective synthesis of trifluorolactic acid, see: b) T. Katagiri, F. Obara, S. Toda, K. Furuhashi, Synlett 1994, 507.
25. 3,3,3-Trichloro-1,2-propanediol has been prepared by hydrolysis of (trichloromethyl)oxirane, see: K. Itoh, S. Sakai, Y. Ishii, J. Org. Chem. 1967, 32, 2210.
26. rac-4, see: a) ref. [15a]; b) I. L. Kunyants, E. Y. Pervova, V. V. Tyuleneva, Izv. Akad. Nauk. SSSR Otdel. Khim. Nauk. 1956, 843; c) F. Arndt, B. Eistert, Ber. 1928, 61, 1121; d) R. M. Groth, J. Org. Chem. 1960, 25, 102.
27. rac-4, see: a) ref. [15a]; b) I. L. Kunyants, E. Y. Pervova, V. V. Tyuleneva, Izv. Akad. Nauk. SSSR Otdel. Khim. Nauk. 1956, 843; c) F. Arndt, B. Eistert, Ber. 1928, 61, 1121; d) R. M. Groth, J. Org. Chem. 1960, 25, 102.
28. rac-4, see: a) ref. [15a]; b) I. L. Kunyants, E. Y. Pervova, V. V. Tyuleneva, Izv. Akad. Nauk. SSSR Otdel. Khim. Nauk. 1956, 843; c) F. Arndt, B. Eistert, Ber. 1928, 61, 1121; d) R. M. Groth, J. Org. Chem. 1960, 25, 102.
29. rac-4, see: a) ref. [15a]; b) I. L. Kunyants, E. Y. Pervova, V. V. Tyuleneva, Izv. Akad. Nauk. SSSR Otdel. Khim. Nauk. 1956, 843; c) F. Arndt, B. Eistert, Ber. 1928, 61, 1121; d) R. M. Groth, J. Org. Chem. 1960, 25, 102.
30. For preparations of scalemic 4, see: a) K. Furuhashi, K. Takai, M. Shintani, JP 61 202697, 1985; b) Bio Research Center Co., JP 59 216594, 1983; c) T. Kubota, H. Shirakura, T. Tanaka, J. Fluorine Chem. 1991, 54, 286; d) C. von dem Bussche-Hünnefeld, C. Cescato, D. Seebach, Chem. Ber. 1992, 125, 2795; e) P. V. Ramachandran, B. Gong, H. C. Brown, J. Org. Chem. 1995, 60, 41.
31. For preparations of scalemic 4, see: a) K. Furuhashi, K. Takai, M. Shintani, JP 61 202697, 1985; b) Bio Research Center Co., JP 59 216594, 1983; c) T. Kubota, H. Shirakura, T. Tanaka, J. Fluorine Chem. 1991, 54, 286; d) C. von dem Bussche-Hünnefeld, C. Cescato, D. Seebach, Chem. Ber. 1992, 125, 2795; e) P. V. Ramachandran, B. Gong, H. C. Brown, J. Org. Chem. 1995, 60, 41.
32. For preparations of scalemic 4, see: a) K. Furuhashi, K. Takai, M. Shintani, JP 61 202697, 1985; b) Bio Research Center Co., JP 59 216594, 1983; c) T. Kubota, H. Shirakura, T. Tanaka, J. Fluorine Chem. 1991, 54, 286; d) C. von dem Bussche-Hünnefeld, C. Cescato, D. Seebach, Chem. Ber. 1992, 125, 2795; e) P. V. Ramachandran, B. Gong, H. C. Brown, J. Org. Chem. 1995, 60, 41.
33. For preparations of scalemic 4, see: a) K. Furuhashi, K. Takai, M. Shintani, JP 61 202697, 1985; b) Bio Research Center Co., JP 59 216594, 1983; c) T. Kubota, H. Shirakura, T. Tanaka, J. Fluorine Chem. 1991, 54, 286; d) C. von dem Bussche-Hünnefeld, C. Cescato, D. Seebach, Chem. Ber. 1992, 125, 2795; e) P. V. Ramachandran, B. Gong, H. C. Brown, J. Org. Chem. 1995, 60, 41.
34. For preparations of scalemic 4, see: a) K. Furuhashi, K. Takai, M. Shintani, JP 61 202697, 1985; b) Bio Research Center Co., JP 59 216594, 1983; c) T. Kubota, H. Shirakura, T. Tanaka, J. Fluorine Chem. 1991, 54, 286; d) C. von dem Bussche-Hünnefeld, C. Cescato, D. Seebach, Chem. Ber. 1992, 125, 2795; e) P. V. Ramachandran, B. Gong, H. C. Brown, J. Org. Chem. 1995, 60, 41.
35. The high volatility of low molecular weight epoxides makes working with them difficult. In addition to reduced volatility, the corresponding cyclic sulfates are more reactive towards most nucleophiles.
36. For a review on the use of cyclic sulfates as epoxide synthons, see: B. B. Lohray, Synthesis 1992, 1035.
37. 3 was achieved at low temperature (-90°C); a) R. W. Hoffmann, H. C. Stiasny, Tetrahedron Lett. 1995, 36, 4595; b) H. C. Stiasny, Synthesis 1996, 259. The reaction of dianions of diols with N,N-sulfuryldiimidazole yields cyclic sulfates, although use of strong base (NaH) is required, see: T. J. Tewson, M. Soderlind, J. Carbohydr. Chem. 1985, 4, 529.
38. 3 was achieved at low temperature (-90°C); a) R. W. Hoffmann, H. C. Stiasny, Tetrahedron Lett. 1995, 36, 4595; b) H. C. Stiasny, Synthesis 1996, 259. The reaction of dianions of diols with N,N-sulfuryldiimidazole yields cyclic sulfates, although use of strong base (NaH) is required, see: T. J. Tewson, M. Soderlind, J. Carbohydr. Chem. 1985, 4, 529.
39. 3 was achieved at low temperature (-90°C); a) R. W. Hoffmann, H. C. Stiasny, Tetrahedron Lett. 1995, 36, 4595; b) H. C. Stiasny, Synthesis 1996, 259. The reaction of dianions of diols with N,N-sulfuryldiimidazole yields cyclic sulfates, although use of strong base (NaH) is required, see: T. J. Tewson, M. Soderlind, J. Carbohydr. Chem. 1985, 4, 529.
40. a) S. J. Brandes, J. A. Katzenellenbogen, Mol. Pharmacol. 1988, 32, 391;
41. b) Y. Gao, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 7538.
42. a) T. J. Tewson, J. Org. Chem. 1983, 48, 3507;
43. b) M. S. Berridge, M. P. Franceschini, E. Rosenfeld, T. J. Tewson, ibid. 1990, 55, 1211;
44. c) P. A. M. van der Klein, G. J. P. H. Boons, G. H. Veeneman, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 1989, 30, 5477.
45. 2-PYR afforded ent-2b in 63% ee, which also crystallized to enantiopurity.
46. Analytically and enantiomerically pure 3 is obtained by distillation under reduced pressure and is an oil at room temperature (cf. rar-3, m.p. 34-35°C).
47. 3 and pyridine or other solvents (e.g. EtOAc) gave inferior results.
48. For a synthesis of enantiopure 7, see: K. P. M. Vanhessche, Z.-M. Wang, K. B. Sharpless, Tetrahedron Lett. 1994, 35, 3469.
49. 2-PYR, afforded ent-2c in 77% ee (which is also raised to enantiopurity by one recrystallization).
50. 2 at -20°C afforded 15 in one step (Scheme 4), albeit in only 40% yield. (Equation Presented)
51. a) W. Reeve, Synthesis 1971, 131;
52. b) J. P. Benner, G. B. Gill, S. J. Parrott, B. J. Wallace, J. Chem. Soc. Perkin 1 1984, 331.
53. a) A. R. Pinder, Synthesis 1980, 425;
54. b) P. N. Rylander, Catalytic Hydrogenation in Organic Syntheses Academic, New York, 1979, p. 235.
55. N. Mitsuo, T. Kunieda, T. Takizawa, J. Org. Chem. 1973, 38, 2255.
56. a) Organic Electrochemistry: an Introduction and a Guide (Eds.: H. Lund, M. M. Baizer), Dekker, New York, 1991;
57. b) T. Shono, Electroorganic Synthesis Academic, London, 1991.
58. M. Nagao, N. Sato, T. Akashi, T. Yoshida, J. Am. Chem. Soc. 1966, 88, 3447.
59. C. Weizmann, M. Sulzbacher, E. Bergmann, J. Am. Chem. Soc. 1948, 70, 1153.
60. a) E. J. Corey, J. O. Link, Tetrahedron Lett. 1992, 33, 3431;
61. b) E. J. Corey, J. O. Link, Y. Shao, ibid. 1992, 33, 3435.
62. 3,3,3-Trichloropropene is prepared by dehydrochlorination of 1,1,1,3-tetrachloropropane, see: R. N. Haszeldine, J. Chem. Soc. 1953, 3371.
63. Smaller quantities (25 g) of 3,3,3-trifluoropropene can also be purchased from Aldrich (for a synthesis, see: R. N. Haszeldine, J. Chem. Soc. 1952, 2504).
64. 6 used. For large scale reactions, a closed system may be employed.
65. E. Huff, Biochim. Biophys. Acta 1961, 48, 506.
66. 23 = -20.1 (c = 1.4 in MeOH) [lit.[18e] - 19.5 (c = 1.3 in MeOH)].