Neighboring lithium-assisted [1,2]-wittig rearrangement: Practical access to diarylmethanol-based 1,4-diols and optically active binol derivatives with axial and sp3-central chirality

Chemistry - A European Journal

Volumn 17, Issue 9, 2011, Pages 2698-2703

  Gao, Guang ^a   Gua, Feng Lei ^a   Jiang, Jian Xiong ^a   Jiang, Kezhi ^a   Sheng, Chun Qi ^a   Lai, Guo Qiao ^a   Xu, Li Wen ^b  

^a HANGZHOU NORMAL UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

asymmetric synthesis; chirality; chirality transfer; diols; Wittig rearrangement

Indexed keywords

AROMATIC ETHER; ASYMMETRIC SYNTHESIS; BINAPHTHALENES; BINOL DERIVATIVES; CHIRALITY TRANSFER; DIOLS; ENANTIOMERIC EXCESS; OPTICALLY ACTIVE; WITTIG REARRANGEMENT;

CHIRALITY; ENANTIOSELECTIVITY; ETHERS; LITHIUM; STEREOCHEMISTRY;

ENANTIOMERS;

EID: 79951803438     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003111     Document Type: Article

References (52)

1. J. A. Marshall, in Comprehensive Organic Synthesis, Vol3 (Eds.:, B.M. Trost, I. Fleming,), Pergamon, Oxford, 1991, pp. 975-1014
2. K. Tomooka, H. Yamamoto, T. Nakai, Liebigs Ann./Recl. 1997, 1275-1281.
3. G. Wittig, L. Löhmann, Justus Liebigs Ann. Chem. 1942, 550, 260-268.
4. T. Nakai, K. Mikami, Chem. Rev. 1986, 86, 885-902
5. M. Kitamura, Y. Hirokawa, N. Maezaki, Chem. Eur. J. 2009, 15, 9911-9917
6. M. Sasaki, H. Ikemoto, M. Kawahata, K. Yamaguchi, K. Takeda, Chem. Eur. J. 2009, 15, 4663-4666
7. N. C. Giampietro, J. P. Wolf, Angew. Chem. 2010, 122, 2984-2986
8. Angew. Chem. Int. Ed. 2010, 49, 2922-2924.
9. Selected examples
10. K. Tomooka, H. Yamamoto, T. Nakai, J. Am. Chem. Soc. 1996, 118, 3317-3318
11. R. E. Maleczka, Jr., F. Geng, J. Am. Chem. Soc. 1998, 120, 8551-8552
12. K. Tomooka, H. Yamamoto, T. Nakai, Angew. Chem. 2000, 112, 4674-4676
13. Angew. Chem. Int. Ed. 2000, 39, 4500-4502
14. K. Tomooka, M. Kikuchi, K. Igawa, M. Suzuki, P.-H. Keong, T. Nakai, Angew. Chem. 2000, 112, 4676-4679
15. Angew. Chem. Int. Ed. 2000, 39, 4502-4505
16. A. Garbi, L. Allain, F. Chorki, M. Ourvitich, B. Crousse, D. Bonnet-Delpon, T. Nakai, J. P. Bégué, Org. Lett. 2001, 3, 2529-2531
17. J. Barluenga, F. J. Fañanás, R. Sanz, C. Marcos, M. Trabada, Org. Lett. 2002, 4, 1587-1590.
18. K. Tomooka, N. Komine, T. Nakai, Tetrahedron Lett. 1997, 38, 8939-8942
19. O. Kitagawa, S. I. Momose, Y. Yamada, M. Shiro, T. Taguchi, Tetrahedron Lett. 2001, 42, 4865-4868
20. O. Miyata, J. Hashimoto, R. Iba, T. Naito, Tetrahedron Lett. 2005, 46, 4015-4018.
21. S. Yue, J. S. Duncan, Y. Yamamoto, C. R. Hutchinson, J. Am. Chem. Soc. 1987, 109, 1253
22. E. J. Corey, X. M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1995
23. T. Lindberg, Strategies and Tactics in Organic Synthesis, Vol.1, Academic Press, San Diego, 1993
24. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547
25. D. P. Steinhuebel, S. J. Lippard, J. Am. Chem. Soc. 1999, 121, 11762-11772.
26. A. Martin, S. Hubert, B. Andreas, K. Peter, WO 2007/082771
27. Y. Goto, S. Arai-Otsuki, Y. Tachibana, D. Ichikawa, S. Ozaki, H. Takahashi, Y. Iwasawa, O. Okamoto, S. Okuda, H. Ohta, T. Sagara, J. Med. Chem. 2006, 49, 847-849
28. M. Kosaka, S. Sekiguchi, J. Naito, M. Uemura, S. Kuwahara, M. Watanabe, N. Harada, K. Hiroi, Chirality 2005, 17, 218-232
29. L. A. Paquette, M. M. Schulze, D. G. Bolin, J. Org. Chem. 1994, 59, 2043-2051.
30. G. Sagrera, G. Seoane, Synthesis 2009, 4190-4202
31. J. C. Chen, L. J. Huang, S. L. Wu, S. C. Kuo, Y. Y. Ho, C. Y. Hsiang, J. Agric. Food Chem. 2007, 55, 8390-8397
32. J. K. Mishra, G. Panda, J. Comb. Chem. 2007, 9, 321-338
33. R. Somu, H. Boshiff, C. Qiao, M. Eric, C. E. Barry III, C. C. Aldrich, J. Med. Chem. 2006, 49, 31-34.
34. S. I. Kiyooka, T. Tsutsui, T. Kira, Tetrahedron Lett. 1996, 37, 8903-8904
35. M. Schlosser, F. Bailly, J. Am. Chem. Soc. 2006, 128, 16042-16043.
36. Comprehensive Asymmetric Catalysis (Eds.:, E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, New York, 1999
37. G. Q. Lin, Y. M. Li, A. S. C. Chan, Principles and Applications of Asymmetric Synthesis, Wiley, New York, 2001.
38. Recent selected examples
39. D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861-863
40. J. L. Stymiest, V. Bagutski, R. M. French, V. K. Aggarwal, Nature 2008, 456, 778-782
41. D. W. C. MacMillan, Nature 2008, 455, 304-308
42. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao, E. N. Jacobsen, Science 2010, 327, 986-990.
43. M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2210
44. P. KoÄovsk, Å. VyskoÄil, M. SmrÄina, Chem. Rev. 2003, 103, 3213-3245
45. J. M. Brunel, Chem. Rev. 2005, 105, 4233-4274
46. J. M. Brunel, Chem. Rev. 2007, 107, PR 1-45
47. M. Berthod, G. Mignani, G. Woodward, M. Lemaire, Chem. Rev. 2005, 105, 1801-1836
48. M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269-279.
49. G. Stavrakov, M. Keller, B. Breit, Eur. J. Org. Chem. 2007, 5726-5733.
50. L. Qiu, J. Qi, C. C. Pai, S. Chan, Z. Zhou, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 4599-4602
51. L. Qiu, F. Yee Kwong, J. Wu, W. H. Lam, S. Chan, W. Y. Yu, Y. M. Li, R. Guo, Z. Zhou, A. S. C. Chan, J. Am. Chem. Soc. 2006, 128, 5955-5965
52. D. Chen, N. Lu, G. Zhang, S. Mi, Tetrahedron: Asymmetry 2009, 20, 1365-1368.