The Three-Component Reaction of Dicarbomethoxycarbene, Aldehydes, and β-Nitrostyrenes: A Stereoselective Synthesis of Substituted Tetrahydrofurans

Journal of Organic Chemistry

Volumn 69, Issue 4, 2004, Pages 1413-1414

  Nair, Vijay ^a   Mathai, Sindhu ^a   Varma, R Luxmi ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CYCLOADDITION REACTIONS;

STYRENE;

ALDEHYDE; CARBENOID; DIAZONIUM COMPOUND; DICARBOMETHOXYCARBENE; DIMETHYL DIAZOMALONATE; NITROSTYRENE; RUTHENIUM; STYRENE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 1242285006     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035673p     Document Type: Article

References (12)

1. (a) de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4952.
2. (b) Huisgen, R.; de March, P. J. Am. Chem. Soc. 1982, 104, 4953.
3. Reviews: (a) Padwa, A. J. Chin. Chem. Soc. 1993, 40, 97.
4. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
5. (c) McMills, M. C.; Wright, D. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; John Wiley and Sons Inc.: New York, 2003; pp 253-314.
6. (d) Hodgson, D. M.; Pierad, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
7. Alt, M.; Maas, G. Tetrahedron 1994, 50, 7435.
8. Jiang, B.; Zhang, X.; Luo, Z. Org. Lett. 2002, 4, 2453.
9. Doyle, M. P.; Hu, W.; Timmons, D. J. R. Org. Lett. 2001, 3, 933.
10. Nair, V.; Sheela, K. C.; Sethumadhavan, D.; Dhanya, R.; Rath, N. P. Tetrahedron 2002, 58, 10341 and references therein.
11. Nair, V.; Mathai, S.; Nair, S. M.; Rath, N. P. Tetrahedron Lett. 2003, 44, 8407.
12. Chakraborty, T. K.; Das, S.; Raju, T. V. J. Org. Chem. 2001, 66, 4091.