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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.
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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