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Molecules 2011, 16(10), 8815-8832; doi:10.3390/molecules16108815
Article

Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions

* , ,  and *
Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
* Authors to whom correspondence should be addressed.
Received: 17 August 2011 / Revised: 11 October 2011 / Accepted: 12 October 2011 / Published: 20 October 2011
(This article belongs to the Special Issue Multicomponent Reaction)
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Abstract

Diastereoselective Ugi reactions of DMAP-based aldehydes with α-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various α-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino)-3-pyridine-carboxaldehyde delivered 3-substituted DMAP derivatives with moderate to high diastereoselectivity. The combination of α-amino acid and DMAP-based aldehyde is thus important to achieve high diastereoselectivity. Kinetic resolution of a secondary alcohol using a chiral DMAP derivative obtained through these reactions was also examined.
Keywords: multicomponent reaction; Ugi reaction; chiral DMAP; kinetic resolution multicomponent reaction; Ugi reaction; chiral DMAP; kinetic resolution
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Mandai, H.; Irie, S.; Mitsudo, K.; Suga, S. Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions. Molecules 2011, 16, 8815-8832.

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