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Asymmetric Synthesis of an Amino Acid Derivative from Achiral Aroyl Acrylamide by Reversible Michael Addition and Preferential Crystallization
Author(s) -
Kaji Yuki,
Uemura Naohiro,
Kasashima Yoshio,
Ishikawa Hiroki,
Yoshida Yasushi,
Mino Takashi,
Sakamoto Masami
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604207
Subject(s) - crystallization , derivative (finance) , acrylamide , michael reaction , chemistry , polymer chemistry , organic chemistry , catalysis , polymer , copolymer , financial economics , economics
Single‐handed α‐amino acid derivatives were generated from achiral precursors without an external chiral source. Conjugate addition of phenethylamine to an achiral aroyl acrylamide under homogeneous conditions gave the α‐amino amides in quantitative yields, which crystallized as a conglomerate of a P 2 1 crystal system. Dynamic preferential crystallization or attrition‐enhanced deracemization resulted in the formation of enantiomorphic crystals of 99 % ee .