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Chemistry. 2016 Nov 7;22(46):16429-16432. doi: 10.1002/chem.201604207. Epub 2016 Oct 6.

Asymmetric Synthesis of an Amino Acid Derivative from Achiral Aroyl Acrylamide by Reversible Michael Addition and Preferential Crystallization.

Author information

1
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
2
Education Center, Faculty of Engineering, Chiba Institute of Technology, Shibazono, Narashino, Chiba, 275-0023, Japan.
3
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.

Abstract

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 P21 crystal system. Dynamic preferential crystallization or attrition-enhanced deracemization resulted in the formation of enantiomorphic crystals of 99 % ee.

KEYWORDS:

Michael addition; amino amide; asymmetric synthesis; deracemization; dynamic preferential crystallization

PMID:
27608273
DOI:
10.1002/chem.201604207
[Indexed for MEDLINE]

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