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

研究成果: Article査読

23 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)7292-7300
ページ数9
ジャーナルEuropean Journal of Organic Chemistry
2015
33
DOI
出版ステータスPublished - 2015 11 1

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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