Synthesis of planar chiral [2.2]paracyclophane monophosphine ligands and their application in the umpolung allylation of aldehydes

Tetrahedron Asymmetry

Volumn 18, Issue 2, 2007, Pages 251-259

  Zhang, Tang Zhi ^a   Dai, Li Xin ^a   Hou, Xue Long ^a,b  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXY[2.2]PARACYCLOPHANE; ALCOHOL DERIVATIVE; ALDEHYDE; CHLORIDE; CYCLOHEXENE DERIVATIVE; CYCLOHEXYL ACETATE; PARACYCLOPHANE DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHINITE; PROLINE DERIVATIVE; SODIUM DERIVATIVE; SODIUM PROLINATE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; LIGAND BINDING; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 33847138944     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.01.020     Document Type: Article

References (62)

1. In: Gleiter G., and Hopf H. (Eds). Modern Cyclophane Chemistry (2004), Wiley-VCH, Weinheim
2. Diederich F. Cyclophanes (1991), Royal Society of Chemistry, Cambridge
3. For review, see:. Gibson S.E., and Knight J.D. Org. Biomol. Chem. 1 (2003) 1256
4. Wu X.W., Sun W., and Hou X.L. Chinese J. Org. Chem. 23 (2003) 906 in Chinese
5. For some examples:. Pye P.J., Rossen K., Reamer R.A., Tsou N.N., Volante R.P., and Reider P.J. J. Am. Chem. Soc. 119 (1997) 6207
6. Belokon Y., Moscalenko M., Ionnikov N., Yashkina L., Antonov D., Vorontsov E., and Rozenberg V. Tetrahedron: Asymmetry 19 (1997) 3245
7. Vettte A.H., and Berkessel A. Tetrahedron Lett. 39 (1998) 1741
8. Wörsdörfer U., Vögtle F., Glorius F., and Pfaltz A. J. Prakt. Chem. 341 (1999) 445
9. Bolm C., and Kühn T. Synlett 6 (2000) 899
10. Rozenberg V.I., Antonov D.Y., Zhuravsky R.P., Vorontsv E.V., Khrustalev V.N., Ikonnikov N.S., and Belokon Y.N. Tetrahedron: Asymmetry 11 (2000) 2683
11. Burk M.J., Hems W., Herzberg D., Malan C., and Zanotti-Gerosa A. Org. Lett. 2 (2000) 4173
12. Tanji S., Ohno A., Sato I., and Soai K. Org. Lett. 3 (2001) 287
13. Zanotti-Gerosa A., Malan C., and Herzberg D. Org. Lett. 3 (2001) 3687
14. Dahmen S., and Bräse S. Chem. Commun. (2002) 26
15. Dahmen S., and Bräse S. J. Am. Chem. Soc. 124 (2002) 5940
16. Hermanns N., Dahmen S., Bolm C., and Bräse S. Angew. Chem., Int. Ed. 41 (2002) 3692
17. Bolm C., Wenz K., and Raabe G. J. Organomet. Chem. 662 (2002) 23
18. Jiang B., and Zhao X.L. Tetrahedron: Asymmetry 15 (2004) 1141
19. Hitchcocl P.B., Rowlands G.J., and Parmar R. Chem. Commun. (2005) 4219
20. Jiang B., Zhao X.L., and Xu X.Y. Tetrahedron: Asymmetry 16 (2005) 1071
21. Whelligan D.K., and Bolm C. J. Org. Chem. 71 (2006) 4609
22. Lauterwasser F., Vanderheiden S., and Bräse S. Adv. Synth. Cat. 348 (2006) 443
23. Chai Q., Song C., Sun Z.J., Ma Y.D., Ma C.Q., Dai Y., and Andrus M.B. Tetrahedron Lett. 47 (2006) 8611
24. Sugiyama S., Aoki Y., and Ishii K. Tetrahedron: Asymmetry 17 (2006) 2847
25. Hou X.-L., Wu X.-W., Dai L.-X., Cao B.-X., and Sun J. Chem. Commun. (2000) 1195
26. Wu X.-W., Hou X.-L., Dai L.-X., Tao J., Cao B.-X., and Sun J. Tetrahedron: Asymmetry 12 (2001) 529
27. Wu X.-W., Yuan K., Sun W., Zhang M.-J., and Hou X.-L. Tetrahedron: Asymmetry 14 (2003) 107
28. Wu X.-W., Zhang T.-Z., Yuan K., and Hou X.-L. Tetrahedron: Asymmetry 15 (2004) 2357
29. The synthesis of racemic diphenylphosphino[2.2]paracyclophane was reported:. Dyer P.W., Dyson P.J., James S.L., Suman P., Davies J.E., and Martin C.M. Chem. Commun. (1998) 1375
30. Some reviews:. Kagan H.B., and Lagasse F. Chem. Pharm. Bull. (2000) 315
31. Komarov I.V., and Borner A. Angew. Chem., Int. Ed. (2001) 1198
32. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029
33. Guo H.-C., Ding K.-L., and Dai L.-X. Chinese Sci. Bull. (2004) 1575 in Chinese
34. Hayashi T., Konoshi M., Fukushima M., Mise T., Kagotani M., Tajika M., and Kumada M. J. Am. Chem. Soc. 104 (1982) 180
35. Bolm C., Muñiz-Fernández K., Seger A., Raabe G., and Gunther K. J. Org. Chem. 63 (1998) 7860
36. Muñiz-Fernández K., and Bolm C. Chem. Eur. J. 6 (2000) 2309
37. Fu G.C. Acc. Chem. Res. 33 (2000) 412
38. Deng W.-P., You S.-L., Hou X.-L., Dai L.-X., Yu Y.-H., and Xia W. J. Am. Chem. Soc. 123 (2001) 6508
39. You S.-L., Hou X.-L., Dai L.-X., Yu Y.-H., and Xia W. J. Org. Chem. 67 (2002) 4684
40. Dai L.-X., Tu T., You S.-L., Deng W.-P., and Hou X.-L. Acc. Chem. Res. 36 (2003) 659
41. Cram D.J., and Day A.C. J. Org. Chem. 31 (1966) 1227
42. Rozenberg V., Danilova T., Sergeeva E., Vorontsov E., Starilova Z., Korlyukov A., and Hopf H. Eur. J. Org. Chem. (2002) 468
43. For reviews:. Wild S.B. Coord. Chem. Rev. 166 (1997) 291
44. Dupont J., Consorti C.S., and Spencer J. Chem. Rev. 105 (2005) 2527
45. For some examples:. Kerr P.G., Leung P.-H., and Wild S.B. J. Am. Chem. Soc. 109 (1987) 4321
46. Pabel M., Willis A.C., and Wild S.B. Inorg. Chem. 35 (1996) 1244
47. Dunina V.V., and Goloven E.B. Tetrahedron: Asymmetry 6 (1995) 2747
48. Valk J.-M., Claridge T.D.W., Brown J.M., Hibbs D., and Hursthouse M.B. Tetrahedron: Asymmetry 6 (1995) 2597
49. McCarthy M., Goddard R., and Guiry P.J. Tetrahedron: Asymmetry 10 (1999) 2797
50. Dunina V.V., Razmyslova E.D., Gorunova O.N., Livantsov M.V., and Grishin Y.K. Tetrahedron: Asymmetry 16 (2005) 817
51. Leung P.-H., McLaughlin G.M., Martin J.W.L., and Wild S.B. Inorg. Chem. 25 (1986) 3392
52. Yanagisawa A. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis (1999), Springer, Heidelberg Chapter 27
53. Zanoni G., Gladiali S., Marchetti A., Piccinini P., Tredicil I., and Vidari G. Angew. Chem., Int. Ed. 43 (2004) 846
54. Zhu S.-F., Yang Y., Wang L.-X., Liu B., and Zhou Q.-L. Org. Lett. 7 (2005) 2333
55. Howell G.P., Minnaard A.J., and Feringa B.L. Org. Biomol. Chem. 4 (2006) 1278
56. Roberts N.K., and Wild S.B. J. Chem. Soc., Dalton Trans. (1979) 2015
57. Yuan K., Zhang T.-K., and Hou X.L. J. Org. Chem. 70 (2005) 6085
58. Fehring V., Kadyrov R., Ludwig M., Holz J., Selke K., and Haage R. J. Organomet. Chem. 621 (2001) 120
59. Kreis M., Friedmann C.J., and Bräse S. Chem. Eur. J. (2005) 7387
60. Hitchcock P.B., Rowlands G.J., and Parmar R. Chem. Commun. (2005) 4219
61. Weidmann B., Maycock C.D., and Seebach D. Helv. Chimi. Acta (1981) 1552
62. Fürstner A., and Voigtlander D. Synthesis (2000) 959