Synthesis of a C1 symmetric BINOL-terpyridine ligand and highly enantioselective methyl propiolate addition to aromatic aldehydes

Tetrahedron

Volumn 66, Issue 11, 2010, Pages 1990-1993

  Chen, Xi ^a   Chen, Wei ^a   Wang, Li ^a   Yu, Xiao Qi ^a   Huang, De Shun ^a   Pu, Lin ^b  

^a Sichuan University   (China)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ESTER DERIVATIVE; LEWIS BASE; LIGAND; PYRIDINE DERIVATIVE; TITANIUM DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 76449090808     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.058     Document Type: Article

References (38)

1. Selected examples:
2. Midland M.M., Tramontano A., and Cable J.R. J. Org. Chem. 45 (1980) 28-29
3. Molander G.A., and St. Jean Jr. D.J. J. Org. Chem. 67 (2002) 3861-3865
4. Trost B.M., and Ball Z.T. J. Am. Chem. Soc. 126 (2004) 13942-13944
5. Tejedor D., Caria- Tellado F., Marro- Tellado J.J., and de Armas P. Chem.- Eur. J. 9 (2003) 3122-3131
6. Gao G., Wang Q., Yu X.-Q., Xie R.-G., and Pu L. Angew. Chem., Int. Ed. 45 (2006) 122-125
7. Rajaram A.R., and Pu L. Org. Lett. 8 (2006) 2019-2021
8. Yang F., Xi P.-H., Lan J.-B., Xie R.-G., and You J.-S. J. Org. Chem. 72 (2007) 5457-5460
9. Trost B.M., Weiss A.H., and von Wangelin A.J. J. Am. Chem. Soc. 128 (2006) 8-9
10. Lin L., Jiang X., Liu W., Qui L., Xu Z., Xu J., Chan A.S.C., and Wang R. Org. Lett. 9 (2007) 2329-2332
11. Zhong J.-C., Hou S.-C., Bian Q.-H., Yin M.-M., Na R.-S., Zheng B., Li Z.-Y., Liu S.-Z., and Wang M. Chem.- Eur. J. 15 (2009) 3069-3071
12. Turlington M., DeBerardinis A.M., and Pu L. Org. Lett. 11 (2009) 2441-2444
13. Pu L. Tetrahedron 59 (2003) 9873-9886
14. Lu G., Li Y.-M., Li X.-S., and Chan A.S.C. Coord. Chem. Rev. 249 (2005) 1736-1744
15. Frantz D.E., Fässler R., Tomooka C.S., and Carreira E.M. Acc. Chem. Res. 33 (2000) 373-381
16. Selected examples on BINOLs containing Lewis base functions:
17. Qin Y.-C., Liu L., and Pu L. Org. Lett. 7 (2005) 2381-2383
18. Yang F., Wei S., Chen C.-A., Xi P., Yang L., Lan J., Gau H.-M., and You J. Chem.- Eur. J. 14 (2008) 2223-2231
19. Hamashima Y., Sawada D., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 121 (1999) 2641-2642
20. Casas J., Náera C., Sansano J.M., and Saá J.M. Org. Lett. 4 (2002) 2589-2592
21. Brunel J.M. Chem. Rev. 105 (2005) 857-897
22. Chen Y., Yekta S., and Yudin A.K. Chem. Rev. 103 (2003) 3155-3211
23. Denmak S.E., and Fu J.-P. Chem. Rev. 103 (2003) 2763-2794
24. Aspinall H.C. Chem. Rev. 102 (2002) 1807-1850
25. Schubert U.S., Hofmeier H., and Newkome G.R. Modern Terpyridine Chemistry (2006), Wiley-VCH, Weinheim
26. Wong K.M.-C., and Yam V.W.-W. Coord. Chem. Rev. 251 (2007) 2477-2488
27. Bazzicalupi C., Bencini A., Bianchi A., Danesi A., Faggi E., Giorgi C., Santarelli S., and Valtancoli B. Coord. Chem. Rev. 252 (2008) 1052-1068
28. Constable E.C. Chem. Soc. Rev. 36 (2007) 246-253
29. Jiang H., Lee S.J., and Lin W. J. Chem. Soc., Dalton Trans. (2002) 3429-3433
30. Jiang H., Lee S.J., and Lin W. Org. Lett. 4 (2002) 2149-2152
31. Reviews on the Lewis acid-Lewis base multifunctional catalysts:
32. Kanai M., Kato N., Ichikawa E., and Shibasaki M. Synlett (2005) 1491-1508
33. Paull D.H., and Lectka T. Acc. Chem. Res. 41 (2008) 655-663
34. Rowlands G.J. Tetrahedron 57 (2001) 1865-1882
35. Matsunaga S., Das J., Roels J., Vogl E.M., Yamamoto N., Lida T., Yamaguchi K., and Shibasaki M. J. Am. Chem. Soc. 122 (2000) 2252-2260
36. Zhang H., Huang W., and Pu L. J. Org. Chem. 66 (2001) 481-487
37. Ballardini R., Balzani V., Gandolfi M.T., Ishow E., Perkins J., Stoddart F.J., Hsian-Rong Tseng H.-R., and Wenger S. J. Am. Chem. Soc. 124 (2002) 12786-12795
38. KrÖhnke F. Synthesis (1976) 1-24