Stereoselective synthesis of tetralins using cationic cyclisations |
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Authors: | Ruth AppelbeMike Casey Aideen DunneEnrica Pascarella |
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Institution: | Chemistry Department, The Centre for Synthesis and Chemical Biology and The Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Dublin 4, Ireland |
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Abstract: | Tetralins, including the terpene calamenene, were prepared by 6-endo cationic cyclisations, effected by addition of an I(I) reagent to alkenylarenes, followed by reductive deiodination. An activating group on the arene was required for efficient cationic cyclisation. Good diastereoselectivity, relative to a chiral centre in the chain linking the alkene to the arene, was observed, with Z-alkenes giving predominantly 1,4-cis disubstituted tetralins, and E-alkenes giving predominantly 1,4-trans derivatives. Analogous 6-exo cationic cyclisations proved very limited in scope. |
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Keywords: | cationic cyclisations diastereoselective tetralins terpenes pseudopterosins calamenenes |
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