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Catalytic, Asymmetric Mannich-type Reactions of N-Acylimino Esters: Reactivity, Diastereo- and Enantioselectivity, and Application to Synthesis of N-Acylated Amino Acid Derivatives

Shu Kobayashi,* Ryosuke Matsubara, Yoshitaka Nakamura, Hidetoshi Kitagawa and Masaharu Sugiura

*Contribution from the Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyou-ku, Tokyo, 113-0033, Japan, Email: skobayasmol.f.u-tokyo.ac.jp

S. Kobayashi, R. Matsubara, Y. Nakamura, H. Kitagawa, M. Sugiura, J. Am. Chem. Soc., 2003, 125, 2507-2515.

DOI: 10.1021/ja0281840 (free Supporting Information)


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Abstract

In the presence of a catalytic amount of Cu(OTf)2 and a chiral diamine ligand, various N-acylimino esters reacted smoothly with silyl enol ethers and alkyl vinyl ethers to afford the corresponding Mannich-type adducts in high yields with high diastereo- and enantioselectivities. The reaction mechanism is discussed.

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Key Words

β-amino ketones, α-amino acids


ID: J48-Y2003-1340