Highly stereo-and regiocontrolled cyclopentannulation via allylphosphonate conjugate addition and hydroboration-oxidation-elimination. Synthesis of pentalenic acid …
G Agnel, E Negishi
Index: Agnel, Gilbert; Negishi, Ei-ichi Journal of the American Chemical Society, 1991 , vol. 113, # 19 p. 7424 - 7426
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Citation Number: 75
Abstract
M borane in THF. After addition of aqueous NaOAc, 30% H202 was slowly added to the hydroboration mixture, and its temperature was maintained at 50'C for 10-15 min. After extractive workup (aqueous NH&l and ether), the crude product was treated with NaHCO, in refluxing MeOH-H20 (1: I) for 1-3 h. By'H NMR. Isolated yield unless otherwise mentioned. dBy GLC. e 1-(3-Oxocyclopentyl) ethyl.
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