Thermodynamically Controlled 1,3-Asymmetric Induction in an Acyclic System: Equilibration of α-Amino Nitriles Derived from α-Alkylbenzylamines and Aldehydes

DOI: 10.1021/jo00003a061

Source and publish data:

Journal of Organic Chemistry p. 1274 - 1279 (1991)

Update date:2022-08-03

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Authors:

Inaba, Takashi

Fujita, Makoto

Ogura, Katsuyuki

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Article abstract of DOI:10.1021/jo00003a061

Acyclic α-amino nitriles 1, derived from α-alkylbenzylamines 3 and aldehydes 4 via a Strecker-type reaction, readily epimerize in MeOH at the newly emerged asymmetric center α to the cyano group.The equilibrium diastereomeric ratio <(R*,R*)-1>:<(R*,S*)-1>

Full text of DOI:10.1021/jo00003a061

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