What question did this study set out to answer?

To investigate the electronic effects of aromatic fluorine substituents on N-benzylcinchonidinium phase-transfer catalysts during the enantioselective alkylation of a glycine anion equivalent.

November 1, 2002Organic Letters

An Unusual Electronic Effect of an Aromatic-F in Phase-Transfer Catalysts Derived fromCinchona-Alkaloid

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Authors

SJSang‐sup JewSeoul National University MYMi‐Sook YooSeoul National University BJByeong‐Seon JeongYeungnam University

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Implication

Experimental study demonstrates enhanced enantioselective alkylation of glycine derivatives using ortho-fluorinated cinchona-alkaloid catalysts, highlighting the electronic role of aromatic fluorine.

Key Points

To investigate the electronic effects of aromatic fluorine substituents on N-benzylcinchonidinium phase-transfer catalysts during the enantioselective alkylation of a glycine anion equivalent.
Synthesized various N-benzylcinchonidinium quaternary ammonium salts with distinct electronic substituents on the benzyl group.
Screened the catalytic systems in enantioselective phase-transfer alkylation reactions to prepare 12 alpha-alkylated amino acid derivatives.
An ortho-fluoro substituent on the benzyl group of the quaternary ammonium salt substantially enhanced enantioselectivity in the alkylation reaction.
The optimized catalyst, O(9)-allyl-N-2',3',4'-trifluorobenzylhydrocinchonidinium bromide, delivered 12 alpha-alkylated amino acid derivatives with 94% to >99% enantiomeric excess (ee).

Cite This Study

Jew et al. (2002) studied this question.

synapsesocial.com/papers/6a83f49e20cfb2932ffe2c42 https://doi.org/10.1021/ol0267679

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Implication

Experimental study demonstrates enhanced enantioselective alkylation of glycine derivatives using ortho-fluorinated cinchona-alkaloid catalysts, highlighting the electronic role of aromatic fluorine.

An Unusual Electronic Effect of an Aromatic-F in Phase-Transfer Catalysts Derived fromCinchona-Alkaloid

Discussion

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Implication

Key Points

Cite This Study

An Unusual Electronic Effect of an Aromatic-F in Phase-Transfer Catalysts Derived fromCinchona-Alkaloid

Discussion

Member takes

Implication

Key Points

Cite This Study

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