Tandem alkylation-cyclization process via an O,C-dianion |
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| Authors: | April R. Banaag Francis Dhoro Darryl D. Dixon Bradley K. Tokeshi |
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| Affiliation: | a Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii, HI 96822, USA
b The Cancer Research Center of Hawaii, 1236 Lauhala Street, Honolulu, Hawaii, HI 96813, USA |
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| Abstract: | 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 γ 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. |
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| Keywords: | Allene Nazarov Cyclization |
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