Optically active 1,1′-di-tert-butyl-2,2′-dibenzophosphetenyl: A highly strained P-stereogenic diphosphine ligand

Tetrahedron Asymmetry

Volumn 15, Issue 14, 2004, Pages 2213-2218

  Imamoto, Tsuneo ^a   Crépy, Karen V L ^a   Katagiri, Kosuke ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; BENZENE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CRYSTALLIZATION; DIMERIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; OXIDATION; PRIORITY JOURNAL; X RAY ANALYSIS;

EID: 3843153036     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.05.041     Document Type: Article

References (28)

1. For representative reviews and accounts, see: Tang W., Zhang X. Chem. Rev. 103:2003;3029-3069
2. Ohkuma T., Kitamura M., Noyori R. Ojima I. Catalytic Asymmetric Synthesis. 2nd ed.:2000;Wiley-VCH, Weinheim. Chapter 1
3. Brown J.M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. 1:1999;Springer, Berlin. Chapter 5.1
4. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;John Wiley & Sons, New york
5. Burk M.J., Feaster J.E., Nugent W.A., Harlow R.L. J. Am. Chem. Soc. 115:1993;10125-10138
6. Jiang Q., Jiang Y., Xiao D., Cao P., Zhang X. Angew. Chem., Int. Ed. 3:1998;1100
7. Robin F., Mercier F., Ricard L., Mathey F., Spagnol M. Chem. Eur. J. 3:1997;1365-1369
8. Yamanoi Y., Imamoto T. J. Org. Chem. 64:1999;2988-2989
9. Tang W., Zhang X. Angew. Chem., Int. Ed. 41:2002;1612-1614
10. Tang W., Zhang X. Org. Lett. 4:2002;4159
11. Tang W., Zhang X. Org. Lett. 5:2003;205
12. Imamoto T. Pure Appl. Chem. 73:2001;373-376
13. Crépy K.V.L., Imamoto T. Top. Curr. Chem. 229:2003;1-40
14. Crépy K.V.L., Imamoto T. Adv. Synth. Catal. 345:2003;79-101
15. It should be noted that TangPhos, (1S,1′S,2R,2′R)-1,1′- di-tert-butyl-2,2′-diphospholanyl, is a well designed chiral phosphine ligand for the formation of a very rigid metal complex and in fact it is successfully applied in highly enantioselective Rh-catalyzed hydrogenations. See: Ref. 6
16. de Boer H.J.R., Akkerman O.S., Bickelhaupt F. J. Organomet. Chem. 321:1987;291-306
17. de Boer H.J.R., van de Heisteeg B.J.J., Schat G., Akkerman O.S., Bickelhaupt F. J. Organomet. Chem. 346:1988;197-200
18. Patzke B., Stanger A. Organometallics. 15:1996;2633-2639
19. Naumann K., Zon G., Mislow K. J. Am. Chem. Soc. 91:1969;7012-7023
20. DeBruin K.E., Zon G., Naumann K., Mislow K. J. Am. Chem. Soc. 91:1969;7027-7030
21. Marinetti A., Carmichael D. Chem. Rev. 102:2002;201-230
22. The enantiomer of complex 4 was also prepared from (R,R)-1 and used in the hydrogenation of MAC. The observed enantioselectivity in this case was 94%
23. Meienza F., Spindler F., Thommen M., Pugin B., Malan C., Mezzetti A. J. Org. Chem. 67:2002;5239-5249
24. Imamoto T., Watanabe J., Wada Y., Masuda H., Yamada H., Tsuruta H., Matsukawa S., Yamaguchi K. J. Am. Chem. Soc. 120:1998;1635-1636
25. Gridnev I.D., Yamanoi Y., Higashi N., Tsuruta H., Yasutake M., Imamoto T. Adv. Synth. Catal. 343:2001;118-136
26. Imamoto, T.; Nagata, K. Unpublished results
27. Tsuruta H., Imamoto T. Tetrahedron: Asymmetry. 10:1999;877-882
28. Gridnev I.D., Higashi N., Imamoto T. Organometallics. 20:2001;4542-4553