Enantioselecitve elimination of Pd-H from η 3-allylpalladium- tol BINAP complexes. Evidence of Syn elimination pathway

Chemistry Letters

Volumn 36, Issue 11, 2007, Pages 1338-1339

  Ogawa, Ryohei ^a   Shigemori, Yusuke ^a   Uehara, Koichi ^a   Sano, Jiro ^a   Nakajima, Takayuki ^a   Shimizu, Isao ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 36849019449     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.1338     Document Type: Article

References (20)

1. For reviews, see: a) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395.
2. b) J. M. Williams, Synlett 1996, 705.
3. c) T. Hayashi, J. Organomet. Chem. 1999, 576. 195.
4. d) G. Helmchen, J. Organomet. Chem. 1999, 576, 203.
5. a) T. Hayashi, K. Kishi, Y. Uozumi, Tetrahedron: Asymmetry 1991, 2, 195.
6. b) E. B. Koroleva, P. G. Andersson, Tetrahedron: Asymmetry 1996, 7, 2467.
7. c) P. G. Andersson, S. Schab, Organometallics 1995, 14, 1.
8. I. Shimizu, Y. Matsumoto, K. Shoji, T. Ono, A. Satake, A. Yamamoto, Tetrahedron Lett. 1996, 37, 7115.
9. The complex S was prepared according to the Jones's method. D. N. Jones, S. D. Knox, J. Chem. Soc., Chem. Commun. 1975, 165.
10. Isomerization between (S)- and (R)-2 was scarcely observed under these condition.
11. 1{H) NMR spectrum.
12. a) J. M. Takacs. E. C. Lawson, F. Clement, J. Am. Chem. Soc. 1997, 119, 5956.
13. b) J. M. Takacs, F. Clement, J. Zhu, S. Chandramouli, X. Gong, J. Am. Chem. Soc. 1997, 119, 5804.
14. Halide effect in the elimination is not unambiguous. For a review, see: K. Fagnou, M. Lautens, Angew. Chem., Int. Ed. 2002, 41, 26.
15. The ratios of 2a:2b:2c were calculated by ' H NMR spectra and GLC using a chiral column.
16. The large deuterium effect in anti elimination is described in Ref. 6a.
17. a) F. Ozawa, T. Ito, A. Yamamoto, J. Am. Chem. Soc. 1980, 102, 6457.
18. b) R. L. Brainard, G. M. Whitesides, Organometallics 1985, 4, 1550.
19. c) R. Romeo, G. Alibrandi, L. M. Scolaro, Inorg. Chem. 1993, 32, 4688.
20. d) J. Evans, J. Schwartz, P. W. Urquhart, J. Organomet. Chem. 1974. 81, C37.