A catalytic strategy was developed for asymmetric substitution reactions at sp -hybridized carbon atoms by using a chiral alkylating agent generated in situ from trichloroacetimidate and a chiral phosphoric acid. The resulting chiral p-methoxybenzyl phosphate selectively reacts with β-amino alcohols rather than those without a β-NH functionality. The use of an electronically and sterically tuned chiral phosphoric acid enables the kinetic resolution of amino alcohols through p-methoxybenzylation with good enantioselectivity.

A Brønsted-acid-catalyzed intramolecular enantioselective SN 2' reaction was developed utilizing trichloroacetimidate as a leaving group. The findings indicated that dual activation of the substrates is operative. This metal-free allylic alkylation allows highly enantioselective access to 2-vinylpyrrolidines bearing various substituents.

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AB r ønsted-acid-catalyzed intramolecular enantioselective S N 2' reaction was developed utilizing trichloroacetimidate as al eaving group.T he findings indicated that dual activation of the substrates is operative.This metal-free allylic alkylation allows highly enantioselective access to 2-vinylpyrrolidines bearing various substituents.

Ac atalytic strategy was developed for asymmetric substitution reactions at sp 3 -hybridized carbon atoms by using ac hiral alkylating agent generated in situ from trichloroacetimidate and ac hiral phosphoric acid. The resulting chiral pmethoxybenzyl phosphate selectively reacts with b-amino alcohols rather than those without a b-NH functionality.T he use of an electronically and sterically tuned chiral phosphoric acid enables the kinetic resolution of amino alcohols through p-methoxybenzylation with good enantioselectivity.