ol7b03349_si_001.pdf (7.13 MB)
Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes
journal contribution
posted on 2017-12-14, 15:44 authored by Truong
N. Nguyen, Jeremy A. MayGaCl3 and
(IPr)GaCl3/AgSbF6 formed
γ-tertiary and γ-quaternary carbons via homoconjugate
addition of organoboron nucleophiles to diester- and ketone-functionalized
cyclopropanes. Electron donor group cyclopropane substituents were
not needed, allowing electron-deficient aryl, alkenyl, alkyl, and
hydrogen-substituted cyclopropanes to be used. The catalytic conditions
were compatible with alkenyl, alkynyl, and aryl nucleophiles, including
ortho-substituted aromatics, to synthesize highly hindered quaternary
carbons. Alkynyl nucleophiles formed substituted cyclopentenes. A
control experiment supports an intermediate carbocation in quaternary
carbon center formation.
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Keywords
aryl nucleophilesquaternary carbon center formationorganoboron nucleophilesortho-substituted aromaticsquaternary carbonshydrogen-substituted cyclopropaneshomoconjugate additionAlkynyl nucleophileselectron donor group cyclopropane substituentscontrol experimentketone-functionalized cyclopropanesalkenylγ- quaternary carbonsQuaternary Carbon Formationelectron-deficient arylGallium-Catalyzed Nucleophilic AdditionCyclopropanes GaCl 3
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