Journal
TETRAHEDRON
Volume 65, Issue 28, Pages 5577-5587Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.01.119
Keywords
Silylated thioacetals; Carbanions; Esters; Carbocycles; Domino reaction
Categories
Funding
- Deutsche Forschungsgemeinschaft [231/11]
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The reaction Of silyl-substituted carbanion 1b with arene-1,2-dicarboxylates 6, 15 yields indenone derivatives 11, 16 in a domino process involving silyl C -> O migration and elimination. However, in a competing pathway, the initial addition of 1b leads to lactone formation (8, 17). Substrates 26, 38 containing an ester group and a bromine substituent react with 1b under Substitution of the halogen not allowing silyl migration. But desilylation with TBAF gives reactive carbanions providing benzo-annulated cycloalkanones 29, 40. (C) 2009 Elsevier Ltd. All rights reserved.
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