Asymmetric hydrogenation of 1,4,5,6-tetrahydropyrazine-2-(N-tert- butyl)carboxamide catalyzed by trans-chelating chiral diphosphine-rhodium complexes

R. Kuwano, Y. Ito

研究成果: Contribution to journalArticle査読

46 被引用数 (Scopus)

抄録

Highly enantioselective hydrogenation of 1,4,5,6-tetrahydropyrazine-2- (N-tert-butyl)carboxamide (2) was accomplished by a rhodium complex coordinated with a chiral diphosphine TRAP ligand, which is possible to chelate to a transition metal atom in a trans-manner. Of particular interest is that (R,R)-(S,S)-i-BuTRAP gave 97% ee of the corresponding piperazine-2- carboxylic acid derivative (3) with (S) configuration, while the hydrogenation with (R,R)-(S,S)-MeTRAP-rhodium catalyst provided (R)-3 with up to 85% ee. 31P NMR studies of behavior of i-Bu- and MeTRAP-rhodium catalysts during the reaction suggest that the asymmetric hydrogenation of 2 with TRAPs may involve two competitive reaction pathways, giving their respective enantiomeric products 3.

本文言語英語
ページ(範囲)1232-1237
ページ数6
ジャーナルJournal of Organic Chemistry
64
4
DOI
出版ステータス出版済み - 2 19 1999
外部発表はい

All Science Journal Classification (ASJC) codes

  • 有機化学

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