Planar-Chiral Heterocycles as Ligands in Metal-Catalyzed Processes: Enantioselective Addition of Organozinc Reagents to Aldehydes

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 444-445

  Dosa, Peter I ^a   Ruble, J Craig ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001111641     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962156g     Document Type: Article

References (14)

1. (a) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230-7231.
2. (b) Ruble, J. C.; Latham, H. A.; Fu, G. C., in press.
3. (a) First report of N-coordination of an azaferrocene to a transition metal: Pyshnograeva, N. I.; Setkina, V. N.; Kursanov, D. N. Izv. Akad. Nauk SSSR, Ser. Khim. 1984, 2778-2780.
4. (b) Review of σπ-complexes of five-membered monoheterocycles: Sadimenko, A. P.; Garnovskii, A. D.; Retta, N. Coord. Chem. Rev. 1993, 126, 237-318.
5. (a) Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
6. (b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072.
7. (c) Comprehensive review of the enantioselective addition of organozinc reagents to aldehydes: Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
8. Ishizaki, M.; Fujita, K.-i.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 411-424.
9. 2O/pentane) afforded 28.8 mg (92%) of 1-phenyl-1-propanol, which was acylated with acetic anhydride. Chiral GC analysis of the acetate revealed a 90% ee of the R isomer. Note: The data reported for eqs 1 and 3-7 are the average of two runs, one with each enantiomer of the catalyst.
10. 3).
11. (a) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877-7878.
12. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597-1606.
13. The absolute configuration of 1-(4-fluorophenyl)propanol has not been determined (no literature data are available).
14. 2. For a discussion, see ref 3c, pp 846-847.