Abstract
Synthesized 3-hydroxy- and 3-benzyloxy-1-benzylquinuclidinium salts are in their catalytic activity comparable to benzyl(triethyl)ammonium chloride and are inferior to catalysts of the tetraalkylammonium type.
The asymmety-induced capability of chiral 3-hydroxy-1-alkylquinuclidinium salts is considerably inferior to the asymmetry-induced capability of the conformationally mobile N-benzylquininium chloride, which indicates the dependence of the asymmetric induction on the possibility of the approach of the β-hydroxylic group and the ammonium center of the catalyst in the transition state of the reaction.
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For previous communication, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1836–1843, August, 1989.
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Esikova, I.A., Serebryakov, É.P. Chiral complex-forming agents and trans-phase transfer agents. Russ Chem Bull 38, 1683–1690 (1989). https://doi.org/10.1007/BF00956956
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DOI: https://doi.org/10.1007/BF00956956