Issue 5, 2012
From the journal:

Organic & Biomolecular Chemistry

Self-association free bifunctional thiourea organocatalysts: synthesis of chiral α-amino acids via dynamic kinetic resolution of racemic azlactones†

Joong-Suk Oh,a   Ji-Woong Lee,a   Tae Hee Ryu,a   Jae Heon Leea  and  Choong Eui Song*ab  

* Corresponding authors

a Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon, Jangan, Suwon, Gyeonggi, Korea
E-mail: s1673@skku.edu
Fax: (+82) 31-290-7075

b Department of Energy Science, Sungkyunkwan University, 300 Cheoncheon, Jangan, Suwon, Gyeonggi, Korea

Abstract

Concentration-independent high enantioselectivity in the dynamic kinetic resolution (DKR) of racemic azlactones affording chiral α-aminoesters has been achieved using self-association free thiourea-based dimeric cinchona alkaloid organocatalysts. Detailed experimental studies and single crystal X-ray analysis confirmed that these bifunctional organocatalysts I do not form H-bonded self-aggregates in either solution or solid state.

Graphical abstract: Self-association free bifunctional thiourea organocatalysts: synthesis of chiral α-amino acids via dynamic kinetic resolution of racemic azlactones

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Article information

DOI
https://doi.org/10.1039/C1OB06629C
Article type
Paper
Submitted
24 Sep 2011
Accepted
08 Nov 2011
First published
08 Dec 2011

Org. Biomol. Chem., 2012,10, 1052-1055

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Self-association free bifunctional thiourea organocatalysts: synthesis of chiral α-amino acids via dynamic kinetic resolution of racemic azlactones

J. Oh, J. Lee, T. H. Ryu, J. H. Lee and C. E. Song, Org. Biomol. Chem., 2012, 10, 1052 DOI: 10.1039/C1OB06629C

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