Asymmetric Synthesis of an Amino Acid Derivative from Achiral Aroyl Acrylamide by Reversible Michael Addition and Preferential Crystallization.
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 P21crystal system. Dynamic preferential crystallization or attrition-enhanced deracemization resulted in the formation of enantiomorphic crystals of 99 % ee.
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
Yuki
Y
Kaji
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
Naohiro
N
Uemura
Education Center, Faculty of Engineering, Chiba Institute of Technology, Shibazono, Narashino, Chiba, 275-0023, Japan.
Yoshio
Y
Kasashima
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
Hiroki
H
Ishikawa
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
Yasushi
Y
Yoshida
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
Takashi
T
Mino
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan. sakamotom@faculty.chiba-u.jp.
Masami
http://orcid.org/0000-0001-9489-2641
M
Sakamoto
D020106:Acrylamide / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D020106:Acrylamide
Michael addition; amino amide; asymmetric synthesis; deracemization; dynamic preferential crystallization