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Dirhodium(II)-catalyzed carbonyl ylide generation. Stereoelectronic control in dioxolane formation

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

The combination of ethyl diazoacetate with aryl aldehydes in the presence of copper(I) or rhodium(II) catalysts results in the formation of 1,3-dioxolane products in moderate to good yields. These reactions occur through a pathway that involves ylide intermediates. Catalyst-dependent diastereocontrol is observed and suggests that metal-associated ylides are involved in the product-determining step. The influence of aryl aldehyde substituents has been determined.

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Authors and Affiliations

  1. Department of Chemistry, Trinity University, 78212, San Antonio, Texas, USA

    M. P. Doyle & D. C. Forbes

  2. Department of Chemistry, The University of Arizona, P. O. Box 210041, 85721-0041, Tucson, AZ, USA

    M. P. Doyle, D. C. Forbes & K. R. Xavier

Authors
  1. M. P. Doyle
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  2. D. C. Forbes
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  3. K. R. Xavier
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 961–965, May, 1998.

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Doyle, M.P., Forbes, D.C. & Xavier, K.R. Dirhodium(II)-catalyzed carbonyl ylide generation. Stereoelectronic control in dioxolane formation. Russ Chem Bull 47, 932–935 (1998). https://doi.org/10.1007/BF02498164

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  • DOI: https://doi.org/10.1007/BF02498164

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