Epoxides and aziridines from diazoacetates via ylide intermediates

Organic Letters

Volumn 3, Issue 6, 2001, Pages 933-935

  Doyle, Michael P ^a   Hu, Wenhao ^a   Timmons, Daren J ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AZIRIDINE DERIVATIVE; AZO COMPOUND; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPOXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ACETIC ACIDS; AZIRIDINES; AZO COMPOUNDS; EPOXY COMPOUNDS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0035932589     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015600x     Document Type: Article

References (22)

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3. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley and Sons, Inc.: New York, 1998; Chapter 7. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911. Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
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13. sig = 6.8%). Of the unique reflections, 1855 (52%) were observed >2σ(I). Solution was achieved utilizing direct methods followed by Fourier synthesis with anisotropic displacement parameters for the non-hydrogen atoms. Conventional refinement indices using the 1855 reflections with F > 4σ(F) are R1 = 0.0601, wR2 = 0.1408. The structure was solved using SHELXS in the Bruker SHELXTL (version 5.0) software package.
14. 2 = H) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-151857 and CCDC-151858. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, U.K. (fax: (+44) 1223-336-033; e-mail: deposit© ccdc.cam.ac.uk).
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16. 3 281.1178, found 281.1177.
17. 3) cut from larger crystal. Data were collected and refined as described for 5. Conventional refinement indices using the 2856 reflections with F > 4σ(F) are R1 = 0.0484, wR2 = 0.1117.
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22. Antilla, J. C.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 5099. Gunnoe, T. B.; White, P. S.; Templeton, J. L.; Casarrubios, L. J. Am. Chem. Soc. 1997, 119, 3171. Rasmussen K. G.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1997, 1287. Nagayama S.; Kobayashi, S. Chem. Lett. 1998, 685. Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 676.