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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
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Received: 17 August 2011; in revised form: 11 October 2011 / Accepted: 12 October 2011 / Published: 20 October 2011
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
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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.
Mandai H, Irie S, Mitsudo K, Suga S. Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions. Molecules. 2011; 16(10):8815-8832.
Mandai, Hiroki; Irie, Shunsuke; Mitsudo, Koichi; Suga, Seiji. 2011. "Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions." Molecules 16, no. 10: 8815-8832.