期刊
TETRAHEDRON
卷 70, 期 39, 页码 7032-7043出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.06.069
关键词
gem-Dihalocyclopropanes; Glycal-derived cyclopropanes; Modified carbohydrates; 2-Branched sugars; Oxepines
资金
- Cancer Society of New Zealand
- Victoria University of Wellington for a Victoria Masters
- Faculty of Science Summer Research Scholarship
The ring opening of 1,2-(gem-dibromo)cyclopropyl carbohydrates by two different modes leads to either 2-C-(bromomethylene)pyranosides (using base) or 2-bromooxepines (using silver salts), as shown previously by us for a D-glucal-derived cyclopropane. The base-promoted ring opening is extended to encompass additional alcohol, thiol and amine nucleophiles, and diastereoisomeric cydopropane precursors. Cross-coupling of the 2-C-(bromomethylene)pyranosides leads to extended 2-C-branched pyranosides. Silver-promoted ring expansion of the cyclopropyl carbohydrates in the presence of various alcohols is described. Cross-coupling of the resulting benzyl 2-bromooxepines affords 2-C-substituted oxepines. (C) 2014 Elsevier Ltd. All rights reserved.
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