Journal
TETRAHEDRON
Volume 61, Issue 31, Pages 7538-7545Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.05.067
Keywords
[4+3] cycloadditions; 2-silyloxyacroleins; lewis acid catalysts; reaction mechanisms; DFT calculations
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The mechanism for the Lewis acid induced [4+3] cycloadditions of 2-(trimethylsilyloxy)acrolein with furan has been examined here through DFT calculations at B3LYP/6-31G* level. The mechanism is a three-step process initialized by the nucleophilic attack of furan to the beta-conjugated position of acrolein yielding a zwitterionic intermediate. The key step on the formation of the seven-membered ring is the electrophilic attack of the furan residue to the carbonyl carbon in this intermediate. The endo selectivity experimentally observed is reproduced by the calculations. (c) 2005 Elsevier Ltd. All rights reserved.
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