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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) - maleic acid , pyridine , aspartic acid , derivative (finance) , chemistry , absolute (philosophy) , organic chemistry , amino acid , biochemistry , philosophy , economics , financial economics , copolymer , polymer , epistemology
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.