High diastereoselectivity in intermolecular carbonyl ylide cycloaddition with aryl aldehyde using methyl diazo(trifluoromethyl)acetate

Organic Letters

Volumn 4, Issue 15, 2002, Pages 2453-2455

  Jiang, Biao ^a   Zhang, Xiaobing ^a   Luo, Zhaohui ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038420084     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0200854     Document Type: Article

References (16)

1. (a) Padwa, A.; Austion, D. J. Angew. Chem., Int. Engl. 1994, 33, 1797.
2. (b) Padwa. A. Acc. Chem. Res. 1991, 24, 22.
3. Padwa, A.; Hornbuckle, S. Chem. Rev. 1991, 91, 263.
4. Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, p 1045.
5. (a) de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4952.
6. (b) Huisgen, R.; de March, P. J. Am. Chem. Soc. 1982, 104, 4953.
7. (a) Doyle, M. P.; Forbes, D. C.; Protopopova, M. N.; Stanley, S. A.; Vasbinder, M. M.; Xavier, K. R. J. Org. Chem. 1997, 62, 7210.
8. (b) Doyle, M. P.; Forbes F. C.; Xavier, K. R. Russ. Chem. Bull. 1998, 47, 932
9. (a) Shi, G. Q.; Xu, Y. Y. Chem. Commun. 1989, 607.
10. (b) Shi, G. Q.; Xu, Y. Y. J. Org. Chem. 1990, 55, 3383.
11. (c) Shi, G. Q.; Xu, Y. Y.; Xu, M. Tetrahedron 1991, 47, 1629.
12. (d) Shi, G. Q.; Cao, Z. Y.; Cai, W. L. Tetrahedron 1995, 51, 5011.
13. For example: (a) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441.
14. (b) Taber, D. F.; Hennessy, M. J.; Louey, J. P. J. Org. Chem. 1992, 57, 436.
15. 2 (5 mL) at the rate of 1.0 mL/h under a nitrogen atmosphere at room temperature. After the addition was completed, the reaction mixture was stirred for an additional 2 h. The solvent was removed in vacuo and the residue was subjected to column chromatography on silica gel eluted with petroleum ether (60-90 °C) and ethyl acetate (15:1) to afford 1,3-dioxolane.
16. Alt, M.; Mass, G. Tetrahedron 1994, 50, 7435.