Journal
TETRAHEDRON
Volume 71, Issue 18, Pages 2636-2642Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.03.042
Keywords
Fulvene; Michael addition; Chalcone; 1,2-Dihydropentalene; Iminium ions
Categories
Funding
- National Institutes of Health [SC1GM082340]
- National Science Foundation [CHE-1011771, CHE-1300817]
- Turkish Scientific and Technological Research Council (TUBITAK) [BIDEP-2219]
- [DBI-0521342]
- [DUE-9451624]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1300817] Funding Source: National Science Foundation
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A systematic study of the reactions of cydopentadiene with alpha,beta-unsaturated carbonyl compounds in the presence of catalytic pyrrolidine-H2O revealed that the reactions can either proceed with a Michael attack at the beta-carbon of enone, or 1,2-addition to the carbonyl, leading either to 4-cyclopentadienyl-2-butanones or 6-vinylfulvenes. The former can be isolated and/or converted to the corresponding 1,2-dihydropentalenes with base (or in one-pot at longer reaction times). Substitution pattern on the enones on the competing pathways have been studied and consistent mechanisms are proposed. (C) 2015 Elsevier Ltd. All rights reserved.
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