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https://hdl.handle.net/10356/102854
Title: | Gold-catalyzed [2+2+1] cycloaddition of 1,6-diyne carbonates and esters with aldehydes to 4-(cyclohexa-1,3-dienyl)-1,3-dioxolanes | Authors: | Rao, Weidong Chan, Philip Wai Hong |
Keywords: | DRNTU::Science::Chemistry | Issue Date: | 2014 | Source: | Rao, W., & Chan, P. W. H. (2014). Gold-Catalyzed [2+2+1] Cycloaddition of 1,6-Diyne Carbonates and Esters with Aldehydes to 4-(Cyclohexa-1,3-dienyl)-1,3-dioxolanes. Chemistry - A European Journal, 20(3), 713-718. | Series/Report no.: | Chemistry - a European journal | Abstract: | A synthetic method to stereoselectively prepare 4-(cyclohexa-1,3-dienyl)-1,3-dioxolanes in good to excellent yields by gold(I)-catalyzed [2+2+1] cycloaddition of 1,6-diyne carbonates and esters with aldehydes is described. The cascade process involves 1,2-acyloxy migration followed by cyclopropenation and cycloreversion. This leads to an unprecedented [2+2+1] cycloaddition of the resulting alkenylgold carbenoid species, examples of which are extremely rare, with two aldehyde molecules at catalyst loadings as low as 1 mol %. The usefulness of this cycloisomerization chemistry was further demonstrated by the transformation of one example to the corresponding phenol. | URI: | https://hdl.handle.net/10356/102854 http://hdl.handle.net/10220/19140 |
ISSN: | 0947-6539 | DOI: | 10.1002/chem.201303685 | Rights: | © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | Fulltext Permission: | none | Fulltext Availability: | No Fulltext |
Appears in Collections: | SPMS Journal Articles |
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