A tandem semipinacol rearrangement/alkylation of α-epoxy alcohols: An efficient and stereoselective approach to multifunctional 1,3-diols

Angewandte Chemie - International Edition

Volumn 43, Issue 13, 2004, Pages 1702-1705

  Hu, Xiang Dong ^a   Fan, Chun An ^a   Zhang, Fu Min ^a   Qiang Tu, Yong ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Alkylation; Allylation; Boron; Rearrangement; Substituent effect

Indexed keywords

ALCOHOLS; CARBON; STEREOCHEMISTRY;

CARBON ATOMS; STEREOCENTERS; TANDEM SEMIPINACOL;

ALKYLATION;

ALCOHOL DERIVATIVE; CARBON; HYDROXYL GROUP;

ALKYLATION; ALLYLATION; ARTICLE; ATOM; CHEMICAL REACTION; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ALCOHOLS; ALKYLATION; EPOXY COMPOUNDS; KETONES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 4043081489     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353177     Document Type: Article

References (53)

1. Y. Hirasawa, H. Morita, M. Shiro, J. Kobayashi, Org. Lett. 2003, 5, 3991.
2. a) T. Saito, T. Suzuki, M. Morimoto, C. Akiyama, T. Ochiai, K. Takeuchi, T. Matsumoto, K. Suzuki, J. Am. Chem. Soc. 1998, 120, 11633;
3. b) B. M. Trost, O. R. Thiel, H. C. Tsui, J. Am. Chem. Soc. 2003, 125, 13155.
4. a) J. D. Winkler, M. B. Rouse, M. F. Greaney, S. J. Harrison, Y. T. Jeon, J. Am. Chem. Soc. 2002, 124, 9726;
5. b) K. Tanino, K. Onuki, K. Asano, M. Miyashita, T. Nakamura, Y. Takahashi, I. Kuwajima, J. Am. Chem. Soc. 2003, 125, 1498.
6. For recent reviews on the stereoselective construction of a quaternary carbon center, see: a) K. Fuji, Chem. Rev. 1993, 93, 2037;
7. b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402; Angew. Chem. Int. Ed. 1998, 37, 388;
8. b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402; Angew. Chem. Int. Ed. 1998, 37, 388;
9. c) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725; Angew. Chem. Int. Ed. 2001, 40, 4591.
10. c) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725; Angew. Chem. Int. Ed. 2001, 40, 4591.
11. For a review of the synthesis of the synthetic building blocks containing three contiguous stereocenters, see: R. W. Hoffmann, Angew. Chem. 1987, 99, 503; Angew. Chem. Int. Ed. Engl. 1987, 26, 489.
12. For a review of the synthesis of the synthetic building blocks containing three contiguous stereocenters, see: R. W. Hoffmann, Angew. Chem. 1987, 99, 503; Angew. Chem. Int. Ed. Engl. 1987, 26, 489.
13. a) Y. Q. Tu, L. D. Sun, P. Z. Wang, J. Org. Chem. 1999, 64, 629;
14. b) C. A. Fan, B. M. Wang, Y. Q. Tu, Z. L. Song, Angew. Chem. 2001, 113, 3995; Angew. Chem. Int. Ed. 2001, 40, 3877;
15. b) C. A. Fan, B. M. Wang, Y. Q. Tu, Z. L. Song, Angew. Chem. 2001, 113, 3995; Angew. Chem. Int. Ed. 2001, 40, 3877;
16. c) D. R. Li, W. J. Xia, Y. Q. Tu, F. M. Zhang, L. Shi, Chem. Commun. 2003, 798;
17. d) C. A. Fan, X. D. Hu, Y. Q. Tu, B. M. Wang, Z. L. Song, Chem. Eur. J. 2003, 9, 4301;
18. e) X. Li, B. Wu, X. Z. Zhao, Y. X. Jia, Y. Q. Tu, D. R. Li, Synlett 2003, 623.
19. For reviews of allylmetal and allenylmetal chemistry, see: a) R. W. Hoffmann, Angew. Chem. 1982, 94, 569; Angew. Chem. Int. Ed. Engl. 1982, 21, 555;
20. For reviews of allylmetal and allenylmetal chemistry, see: a) R. W. Hoffmann, Angew. Chem. 1982, 94, 569; Angew. Chem. Int. Ed. Engl. 1982, 21, 555;
21. b) Y. Yamamoto, K. Maruyama, Heterocycles 1982, 18, 357;
22. c) K. Furuta, M. Ishiguro, R. Haruta, N. Ikeda, H. Yamamoto, Bull. Chem. Soc. Jpn 1984, 57, 2768;
23. d) R. W. Hoffmann, T. Sander, Chem. Ber. 1990, 123, 145;
24. e) S. E. Denmark, J. P. Fu, Chem. Rev. 2003, 103, 2763;
25. f) J. W. J. Kennedy, D. G. Hall, Angew. Chem. 2003, 115, 4880; Angew. Chem. Int. Ed. 2003, 42, 4732.
26. f) J. W. J. Kennedy, D. G. Hall, Angew. Chem. 2003, 115, 4880; Angew. Chem. Int. Ed. 2003, 42, 4732.
27. a) E. D. Mihelich, Tetrahedron Lett. 1979, 20, 4729;
28. b) C. M. Marson, A. J. Walker, J. Pickering, A. D. Hobson, R. Wrigglesworth, S. J. Edge, J. Org. Chem. 1993, 58, 5944.
29. H. C. Brown, U. S. Racherla, P. J. Rellechia, J. Org. Chem. 1990, 55, 1868.
30. 1H NMR NOE experiments are shown in the Supporting Information.
31. CCDC-223949 (2 f) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge by accessing www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; of deposit@ ccdc.cam.ac.uk).
32. L. A. Paquette, F. Geng, Org. Lett. 2002, 4, 4547.
33. C. K. Sha, K. C. Santhosh, S. H. Lih, J. Org. Chem. 1998, 63, 2699.
34. C. Iwata, Y. Takemoto, M. Doi, T. Imanishi, J. Org. Chem. 1988, 53, 1623.
35. M. C. Pirrung, J. Am. Chem. Soc. 1981, 103, 82.
36. C. E. Schwartz, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 9272.
37. a) G. A. Molander, J. A. McKie, J. Org. Chem. 1995, 60, 872;
38. 2, see: G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307.
39. a) J. L. Moreau in The Chemistry of Ketenes, Allenes, and Related Compounds (Ed.: S. Patai), Wiley, New York, 1980, pp. 363-414;
40. b) N. E. Schore, Chem. Rev. 1988, 88, 1081;
41. c) D. F. Harvey, D. M. Sigano, Chem. Rev. 1996, 96, 271;
42. d) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675;
43. e) I. Beletskaya, C. Moberg, Chem. Rev. 1999, 99, 3435;
44. f) F. Sato, H. Urabe, S. Okamoto, Chem. Rev. 2000, 100, 2835;
45. g) A. J. McCarroll, J. C. Walton, Angew. Chem. 2001, 113, 2282; Angew. Chem. Int. Ed. 2001, 40, 2224.
46. g) A. J. McCarroll, J. C. Walton, Angew. Chem. 2001, 113, 2282; Angew. Chem. Int. Ed. 2001, 40, 2224.
47. For the preparation of allenylboronic acid, see: N. Ikeda, I. Arai, H. Yamamoto, J. Am. Chem. Soc. 1986, 108, 483.
48. a) N. L. Allinger, M. T. Tribble, Tetrahedron lett. 1971, 3259;
49. b) R. Amstutz, J. D. Dunitz, D. Seebach, Angew. Chem. 1981, 93, 487; Angew. Chem. Int. Ed. Engl. 1981, 20, 465;.
50. b) R. Amstutz, J. D. Dunitz, D. Seebach, Angew. Chem. 1981, 93, 487; Angew. Chem. Int. Ed. Engl. 1981, 20, 465;.
51. c) W. R. Kenan, J. Mol. Struct. 1985, 126, 385;
52. d) X. X. Xu, H. Q. Dong, J. Org. Chem. 1995, 60, 3039.
53. 2), see: T. Imamoto, M. Ono, Chem. Lett. 1987, 501.