Absolute Asymmetric Synthesis of an Aspartic Acid Derivative from Prochiral Maleic Acid and Pyridine under Achiral Conditions | Zendy

Uemura Naohiro | Zendy; Sano Kento | Zendy; Matsumoto Arisa | Zendy; Yoshida Yasushi | Zendy; Mino Takashi | Zendy; Sakamoto Masami | Zendy

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Absolute Asymmetric Synthesis of an Aspartic Acid Derivative from Prochiral Maleic Acid and Pyridine under Achiral Conditions

Author(s) -

Uemura Naohiro,

Sano Kento,

Matsumoto Arisa,

Yoshida Yasushi,

Mino Takashi,

Sakamoto Masami

Publication year - 2019

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.201901324

Subject(s) - enantioselective synthesis , yield (engineering) , pyridine , maleic acid , crystallization , acetic acid , derivative (finance) , aspartic acid , chemistry , racemization , organic chemistry , catalysis , materials science , amino acid , polymer , copolymer , biochemistry , economics , financial economics , metallurgy

The asymmetric synthesis of an aspartic acid derivative, N ‐succinopyridine, from prochiral starting materials involving dynamic enantioselective crystallization was accomplished without using any external chiral source. The aza‐Michael addition reaction of prochiral maleic acid and pyridine afforded racemic conglomerate N ‐succinopyridine in water. Continuous stirring of the suspension of the reaction mixture with acetic acid promoted gradual deracemization to afford a crystal with an excellent optical purity of 99 % in 71 % yield.

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