Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes

Teppei Otsuki, Jun Kumagai, Yoshihito Kohari, Yuko Okuyama, Eunsang Kwon, Chigusa Seki, Koji Uwai, Yasuteru Mawatari, Nagao Kobayashi, Tatsuo Iwasa, Michio Tokiwa, Mitsuhiro Takeshita, Atushi Maeda, Akihiko Hashimoto, Kana Turuga, Hiroto Nakano

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22 Citations (Scopus)

Abstract

The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical yields (up to 86 %) with excellent diastereoselectivities (endo/exo, up to 96:4) and enantioselectivities (up to 97 % ee). Furthermore, the obtained isoxazolidines were easily converted into γ-amino diols that contain three contiguous stereogenic centers.

Original languageEnglish
Pages (from-to)7292-7300
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number33
DOIs
Publication statusPublished - 2015 Nov 1

Keywords

  • Amino alcohols
  • Cycloaddition
  • Diastereoselectivity
  • Enantioselectivity
  • Nitrogen heterocycles
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Otsuki, T., Kumagai, J., Kohari, Y., Okuyama, Y., Kwon, E., Seki, C., Uwai, K., Mawatari, Y., Kobayashi, N., Iwasa, T., Tokiwa, M., Takeshita, M., Maeda, A., Hashimoto, A., Turuga, K., & Nakano, H. (2015). Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes. European Journal of Organic Chemistry, 2015(33), 7292-7300. https://doi.org/10.1002/ejoc.201500926