Enantioselective ring opening of meso aziridines catalyzed by tridentate Schiff base chromium(III) complexes

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1611-1613

  Li, Zhen ^a   Fernández, Mónica ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOINDANOL; AZIRIDINE DERIVATIVE; CHROMIUM; INDAN DERIVATIVE; SCHIFF BASE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

AZIRIDINES; CATALYSIS; CHROMIUM; INDANS; SCHIFF BASES; STEREOISOMERISM;

EID: 0033581774     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990992h     Document Type: Article

References (15)

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2. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
3. For a recent review of asymmetric aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; 1999; Chapter 17.
4. For examples of desymmetrization of meso aziridines, see: (a) Matsubara, S.; Kodama, T.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6379.
5. (b) Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc., Chem. Commun. 1994, 2699.
6. (c) Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. Tetrahedron 1996, 52, 7817.
7. (d) Müller, P.; Nury, P. Org. Lett. 1999, 1, 439.
8. (a) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
9. (b) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
10. (c) Schaus, S. E.; Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1997, 62, 4197.
11. 3 (1.05 equiv) was added via syringe. The solution was stirred for the appropriate reaction time. Finally, the reaction mixture was concentrated in vacuo and isolation of the pure ring-opened product was accomplished by flash column chromatography on silica gel.
12. For a similar trend in asymmetric hetero-Diels - Alder reactions, see: Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. Angew. Chem. Intl. Ed. Engl.1999, 38, 2398.
13. Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 11, 1693.
14. 3 (2.25 mL, 17 mmol) and was stirred under a nitrogen atmosphere overnight at room temperature. Volatile materials were removed in vacuo. Flash column chromatography (13-20% acetone in hexane) afforded 459 mg (50% yield) of the complex as an air-stable brown solid.
15. Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem. Int. Ed. Engl. 1998, 37, 2580 and references cited herein.