Synthesis 2014; 46(13): 1793-1801
DOI: 10.1055/s-0033-1341125
paper
© Georg Thieme Verlag Stuttgart · New York

Design Aspects of Metal-Free Nitrogen-Based Catalysts and Their Influence on the Yield in the Henry Reaction

Qiong Ji Yao
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2 B1-14, 637459, Singapore   Fax: +65-67947553   Email: zaher@ntu.edu.sg
,
Duc Thinh Khong
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2 B1-14, 637459, Singapore   Fax: +65-67947553   Email: zaher@ntu.edu.sg
,
Qi Gao
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2 B1-14, 637459, Singapore   Fax: +65-67947553   Email: zaher@ntu.edu.sg
,
Zaher M. A. Judeh*
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2 B1-14, 637459, Singapore   Fax: +65-67947553   Email: zaher@ntu.edu.sg
› Author Affiliations
Further Information

Publication History

Received: 01 November 2013

Accepted after revision: 14 March 2014

Publication Date:
17 April 2014 (online)


Abstract

Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction are disclosed. C 1-Symmetric, N,N-1,2-disposed amine-imine type catalysts were found to be most efficient. C 1-N,N-1,2-Disposed 1,2,3,4-tetrahydro-1,1′-biisoquinoline selectively and efficiently catalyzed the addition of nitromethane to α-keto esters and aldehydes giving exclusively the corresponding β-nitro alcohol adducts in excellent yields under very mild conditions.

Supporting Information

 
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