Highly selective stereodivergent synthesis of separable amide rotamers, by using Pd chemistry, and their thermodynamic behavior

Nobutaka Ototake, Masashi Nakamura, Yasuo Dobashi, Haruhiko Fukaya, Osamu Kitagawa

研究成果: Article査読

14 被引用数 (Scopus)

抄録

By using Pd chemistry, a highly selective stereodivergent synthesis of separable amide rotamers was achieved. Allylation of 2,4,6-tri-tert-bu- tylanilides using a π-allyl-Pd catalyst gave N-allylated anilides with moderate-to-excellent Z-rotamer selectivity (ZIE = 3 to > 50). The Z-rotamer selectivity depends considerably on the substituent on the anilide substrates. On the other hand, the E rotamers of N-allylated 2,4,6-tri-tert-butylanilides were obtained with almost complete selectivity (E/Z > 50) through O-allylation of 2,4,6-tri-tert-butylanilides and the subsequent Pd II-catalyzed Claisen rearrangement of the resulting O-allyl imi-date. The prepared anilide rotamers changed to equilibrium mixtures in which the E rotamer was the major isomer when heated in toluene.

本文言語English
ページ(範囲)5090-5095
ページ数6
ジャーナルChemistry - A European Journal
15
20
DOI
出版ステータスPublished - 2009 5 11

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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