Mechanistic and synthetic aspects of hydroboration with a simple atropisomeric ligand prepared from 1-(1′-(isoquinolyl)-2-naphthol

Journal of Organometallic Chemistry

Volumn 680, Issue 1-2, 2003, Pages 329-334

  Korostylev, Andrei ^a   Gridnev, Ilya ^a   Brown, John M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Catecholborane; Enantiomer; Styrene

Indexed keywords

2 NAPHTHOL; BORANE DERIVATIVE; CATECHOL DERIVATIVE; CATION; ISOQUINOLINE DERIVATIVE; LIGAND; NAPHTHOL DERIVATIVE; RHODIUM COMPLEX; STYRENE;

ARTICLE; CATALYST; CONTROLLED STUDY; ELECTRON; ENANTIOMER; HYDROBORATION; ISOMERISM; LOW TEMPERATURE; SYNTHESIS;

EID: 0042890310     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(03)00602-8     Document Type: Article

References (42)

1. Alcock N.W. Brown J.M. Hulmes D.I. Tetrahedron Asymm. 4 1993 743
2. Brown J.M. Hulmes D.I. Guiry P.J. Tetrahedron 50 1994 4493
3. Brown J.M. Hulmes D.I. Layzell T.P. Chem. Commun. 1993 1673
4. Doucet H. Fernandez E. Layzell T.P. Brown J.M. Chem. Eur. J. 5 1999 1320
5. McCarthy M. Hooper M.W. Guiry P.J. Chem. Commun. 2000 1333
6. Fernandez E. Maeda K. Hooper M.W. Brown J.M. Chem. Eur. J. 6 2000 1840
7. Lacey P.M. McDonnell C.M. Guiry P.J. Tetrahedron Lett. 41 2000 2475
8. Segarra A.M. Guerrero R. Claver C. Fernandez E. Chem. Commun. 2001 1808
9. McCarthy M. Guiry P.J. Tetrahedron 57 2001 3809
10. Maeda K. Brown J.M. Chem. Commun. 2002 310
11. Segarra A.M. Guerrero R. Claver C. Fernandez E. Chem. Eur. J. 9 2003 191
12. For recent papers on catalytic asymmetric hydroboration see: S. Demay, F. Volant, P. Knochel, Angew. Chem. Int. Ed. 40 (2001) 1235;
13. F.Y. Kwong, Q.C. Yang, T.C.W. Mak, A.S.C. Chan, K.S. Chan, J. Org. Chem. 67 (2002) 2769
14. A.P. Luna, M. Bonin, L. Micouin, H.P. Husson, J. Am. Chem. Soc. 124 (2002) 14503
15. R.J. Kloetzing, M. Lotz, P. Knochel, Tetrahedron Asymm. 14 (2003) 255
16. S. Gao, X.Q. Hu, Z. Zheng, Prog. Chem. 14 (2002) 438
17. Aplin R.T. Doucet H. Hooper M.W. Brown J.M. Chem. Commun. 1997 2097
18. Doucet H. Brown J.M. Tetrahedron Asymm. 8 1997 3775
19. Nishibayashi Y. Segawa K. Ohe K. Uemura S. Organometallics 14 1995 5486
20. Richards C.J. Hibbs D.E. Hursthouse M.B. Tetrahedron Lett. 36 1995 3745
21. Ahn K.H. Cho C.-W. Baek H.-H. Park J. Lee S. J. Org. Chem. 61 1996 4937
22. Nishibayashi Y. Segawa K. Arikawa Y. Ohe K. Hidai M. Uemura S. J. Organomet. Chem. 545 1997 381
23. Baker M.J. Harrison K.N. Orpen A.G. Pringle P.G. Shaw G. J. Chem. Soc. Chem. Commun. 1991 803
24. Baker M.J. Pringle P.G. J. Chem. Soc. Chem. Commun. 1991 1292
25. Tucker S.C. Brown J.M. Oakes J. Thornthwaite D. Tetrahedron 57 2001 2545
26. Mason S.F. Seal R.H. Roberts D.R. Tetrahedron 30 1974 1671
27. Bunnenberg E. Djerassi C. Mislow K. Moscowitz A. J. Am. Chem. Soc. 84 1962 2823
28. Delapierre G. Brunel J.M. Constantieux T. Buono G. Tetrahedron Asymm. 12 2001 1345
29. Brown J.M. Evans P.L. James A.P. Org. Synth. 68 1989 64
30. Burk M.J. Feaster J.E. Nugent W.A. Harlow R.L. J. Am. Chem. Soc. 115 1993 10125
31. Gridnev I.D. Yasutake M. Higashi N. Imamoto T. J. Am. Chem. Soc. 123 2001 5268
32. Giernoth R. Heinrich H. Adams N.J. Deeth R.J. Bargon J. Brown J.M. J. Am. Chem. Soc. 122 2000 12381
33. Gridnev I.D. Higashi N. Asakura K. Imamoto T. J. Am. Chem. Soc. 122 2000 7183
34. Brown J.M. Lloyd-Jones G.C. J. Am. Chem. Soc. 116 1994 866
35. Musaev D.G. Mebel A.M. Morokuma K. J. Am. Chem. Soc. 116 1994 10693
36. Dorigo A.E. Schleyer P. van R. Angew. Chem. Int. Ed. Engl. 34 1995 115
37. Liedtke J. Ruegger H. Loss S. Grutzmacher H. Angew. Chem. Int. Ed. 39 2000 2478
38. Widauer C. Grutzmacher H. Ziegler T. Organometallics 19 2000 2097
39. M.R. Smith III, Prog. Inorg Chem. 48 (1999) 505; reference 43 in that review describes a closely related complex derived from catechol borane and the bridged Rh DIPPE dihydride: S.A. Westcott, N.J. Taylor, T.B. Marder, R.T. Baker, J.C. Calabrese, unpublished work.
40. See also: D. Curtis, M.J.G. Lesley, N.C. Norman, A.G. Orpen, J. Starbuck, J. Chem. Soc. Dalton Trans. (1999) 1587. We thank Prof. Todd Marder for bringing this work to our attention.
41. Burch R.R. Shusterman A.J. Muetterties E.L. Teller R.G. Williams J.M. J. Am. Chem. Soc. 105 1983 3546
42. Teller R.G. Williams J.M. Koetzle T.F. Burch R.R. Gavin R.M. Muetterties E.L. Inorg. Chem. 20 1981 1806