Intrinsic diastereotopism of geminal protons in quaternary salts from quinuclidine and hexamine

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Abstract
Intrinsic diastereotopism has been demonstrated directly by room-temperature n.m.r. spectroscopy for the geminal ring-methylene protons adjacent to positive nitrogen in quaternary salts derived from quinuclidine or hexamine and suitable chiral alkylating agents (α-phenylethyl bromide and ethyl α-bromo-propionate).