Enantioselective ring opening of aza and oxabicyclic alkenes with dimethylzinc

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1971-1973

  Lautens, Mark ^a   Hiebert, Sheldon ^a   Renaud, Jean Luc ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000563324     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006052a     Document Type: Article

References (15)

1. Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804.
2. (a) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617.
3. (b) Chiu, P.; Lautens, M. Topics Curr. Chem. 1997, 190, 1.
4. Lautens, M. Synlett 1993, 177.
5. For the preparation and use of (4S)-2-(2-(diphenylphosphino)phenyl)-4-isopropyl-1,3-oxazoline (abbreviated as i-Pr-POX) (a) Williams, J. M. J. Synlett 1996, 705 and references therein.
6. (b) Spinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
7. (c) Von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. For a review on oxazolines and bisoxazolines, see:
8. (d) Pfaltz, A. Synlett 1999, 835.
9. For the synthesis of 2(S)-(diphenylphosphino)-1-[4(S)-isopropyl-2-oxazolin-2-yl]ferrocene (abbreviated as (S)-i-Pr-DIPOF) and other ferrocene type ligands, see: (a) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377.
10. (b) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79.
11. (c) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 62, 10.
12. You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun.
13. (a) Lautens, M.; de Frutos, O.; Stammers, T. A. Tetrahedron Lett. 1999, 40, 8317.
14. (b) Lautens, M.; Chiu, P. Tetrahedron Lett. 1993, 34, 773.
15. Lautens, M.; Rovis, T. J. Org. Chem. 1997, 62, 5246.