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Neil G. Almstead ;Journal of the Mexican Chemical Society 2009, 53 (3)

Autor: Scott E. Denmark

Fuente: http://www.redalyc.org/


Introducción



Journal of the Mexican Chemical Society ISSN: 1870-249X editor.jmcs@gmail.com Sociedad Química de México México Denmark, Scott E.; Almstead, Neil G. Stereochemical Studies on the Addition of Allylsilanes to Aldehydes.
The SE´ Component Journal of the Mexican Chemical Society, vol.
53, núm.
3, julio-septiembre, 2009, pp.
174-192 Sociedad Química de México Distrito Federal, México Available in: http:--www.redalyc.org-articulo.oa?id=47512154016 How to cite Complete issue More information about this article Journals homepage in redalyc.org Scientific Information System Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Non-profit academic project, developed under the open access initiative J.
Mex.
Chem.
Soc.
2009, 53(2), 174-192 © 2009, Sociedad Química de México ISSN 1870-249X Article Stereochemical Studies on the Addition of Allylsilanes to Aldehydes. The SE’ Component Scott E.
Denmark* and Neil G.
Almstead 245 Roger Adams Laboratory, Box 18, Department of Chemistry, University of Illinois, 600 S.
Mathews Ave., Urbana, IL 61801, Phone:(217) 333-0066, Fax: (217) 333-3984, sdenmark@illinois.edu Dedicated to the memory of Ernest L.
Eliel, the doyen of stereochemistry Received August 14, 2009; accepted September 30, 2009 Abstract: Model compounds ul-1 and lk-1 have been studied to determine both the position of the silicon electrofuge and the relative orientation of the double bonds in the transition structure of the allylmetal-aldehyde condensation.
The use of the deuterium label allows an unbiased assessment of the syn versus anti SE’ pathways.
The synthesis of configurational proof of model systems ul-1 and lk-1 are discussed as well as the cyclization of the model system.
Cyclization of model 1 was found to proceed with high selectivity via an anti SE’ pathway regardless of the proximal-distal ratio for all Lewis acids studied.
Reactions promoted by fluoride ion favored the proximal product, but both syn and ...





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