Tandem alkylation–cyclization process via an O, C-dianion
…, F Dhoro, B Derrick, DD Dixon, JP Mitchell, BK Tokeshi…
Index: Banaag, April R.; Berger, Gideon O.; Dhoro, Francis; Delos Santos, Derrick B.; Dixon, Darryl D.; Mitchell, James P.; Tokeshi, Bradley K.; Tius, Marcus A. Tetrahedron, 2005 , vol. 61, # 13 p. 3419 - 3428
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Citation Number: 3
Abstract
A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition–deprotonation–alkylation–cyclization process is described. Addition of lithioallene to enamides generates tetrahedral intermediate. 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.
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