A catalytic desymmetrization of strained alkenes by ring-opening of meso-diazabicycles with acyl anion nucleophiles is reported. Densely functionalized trans-1,2-hydrazinoacyl cyclopentene building blocks are obtained stereoselectively. The acyl anion equivalent is generated in situ under very mild conditions from readily available organoboron precursors.
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Ménard et al. (2007) studied this question.
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