Dirhodium(II)-catalyzed carbonyl ylide generation. Stereoelectronic control in dioxolane formation |
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Authors: | M. P. Doyle D. C. Forbes K. R. Xavier |
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Affiliation: | (1) Department of Chemistry, Trinity University, 78212 San Antonio, Texas, USA;(2) Department of Chemistry, The University of Arizona, P. O. Box 210041, 85721-0041 Tucson, AZ, USA |
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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. Current address. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 961–965, May, 1998. |
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Keywords: | carbonyl ylides, metal-associated ylides dipolar addition, rhodium(II) catalysts, cooper(I) hexafluorophosphate ethyl diazoacetate, metal carbenes |
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