Mandai, Hiroki Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID publons researchmap
Irie, Shunsuke Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University
Mitsudo, Koichi Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID publons researchmap
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.
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