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Molecules 2011, 16(10), 8815-8832;

Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions

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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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. View Full-Text
Keywords: multicomponent reaction; Ugi reaction; chiral DMAP; kinetic resolution multicomponent reaction; Ugi reaction; chiral DMAP; kinetic resolution

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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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