Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphide complex

Journal of the American Chemical Society

Volumn 128, Issue 9, 2006, Pages 2786-2787

  Chan, Vincent S ^a   Stewart, Ian C ^a   Bergman, Robert G ^a   Dean Toste, F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; PHOSPHINE DERIVATIVE; RUTHENIUM; TRANSITION ELEMENT;

ALKYLATION; ANALYTIC METHOD; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENANTIOMER; PHASE TRANSITION; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 33644959532     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058100y     Document Type: Article

References (14)

1. Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362.
2. (a) Buhro, W. E.; Zwick, B. D.; Georgiou, S.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 2427-2439.
3. (b) Crisp, G. T.; Salem, G.; Wild, S. B. Organometallics 1989, 8, 2360-2367.
4. (c) Bohle, D. S.; Clark, G. R.; Rickard, C. E. F.; Roper, W. R. J. Organomet. Chem. 1990, 393, 243-285.
5. For a recent review, see: Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1-40.
6. For recent asymmetric syntheses, see: (a) Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950-953.
7. (b) Moncarz, J. R.; Laritcheva, N. F.; Glueck, D. S. J. Am. Chem. Soc. 2002, 124, 13356-13357.
8. Fox, D. J.; Bergman, R. G. Organometallics 2004, 23, 1656-1670.
9. Kaplan, A. W.; Ritter, J. C. M.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 6828-6829.
10. 2 is described in the Supporting Information.
11. The full scope of electrophiles that react with 1 will be reported in due course.
12. Metal phosphide complexes typically exhibit low barriers to pyramidal inversion: Rogers, J. R.; Wagner, T. P. S.; Marynick, D. S. Inorg. Chem. 1994, 33, 3104-3110. We are currently investigating the barrier to pyramidal inversion in 7.
13. Other diphosphine ligands afforded 9 with low or no enantiomeric excess: (R,R)-DIOP (0%); (R,R)-i-Pr-DuPhos (0%): (R,R)-Me-DuPhos (-10%); (R,R)-Et-DuPhos (-9%).
14. By agreement of the authors, this paper should have appeared simultaneously on the ASAP version of the journal with the paper by Scriban and Glueck that immediately follows this one in the paginated version of the journal (Scriban, C.; Glueck, D. S. J. Am. Chem. Soc. 2006, 128, 2788-2789.