Journal
TETRAHEDRON
Volume 61, Issue 13, Pages 3419-3428Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.01.097
Keywords
allene; nazarov; cyclization
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A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition-deprotonation-alkylation-cyclization process is described. Addition of lithioallene 2 to enamides 1 generates tetrahedral intermediate 3. Deprotonation of the gamma carbon atom of the allene function in situ, followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenones 6. (c) 2005 Elsevier Ltd. All rights reserved.
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