Journal
TETRAHEDRON
Volume 66, Issue 1, Pages 321-328Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.10.087
Keywords
Vinyl cyclopropane; Cyclic carbonate; Gold-catalyzed reaction; 6-endo-dig Process
Categories
Funding
- Renmin University of China and National Science Foundation of China [20502033]
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A convenient new method was developed to prepare two types of vinyl cyclopropane derivatives through gold-catalyzed cyclization of 1-alkynyl cyclopropyl tert-butyl carbonates 2. Different from the previous reported 5-exo-dig route, the 6-endo-dig addition is the preferred pathway to provide six-membered cyclized carbonates. Two factors, including stereoelectronic effect and steric effect might affect the regioselectivity. Therefore, low steric aliphatic substrates afforded only six-membered isomers. The synthetic utility of compound 3 was also explored to afford a series of beta-carbonyl cyclopropanol derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
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