Enantioselective electrophilic trifluoromethylation of β-keto esters with Umemoto reagents induced by chiral nonracemic guanidines
- Noritake, Shun
- Shibata, Norio
- Nomura, Yoshinori
- Huang, Yiyong
- Matsnev, Andrej
- Nakamura, Shuichi
- Toru, Takeshi
- Cahard, Dominique
- シバタ, ノリオ
- ナカムラ, シュウイチ
- トオル, タケシ
- 柴田, 哲男
- 中村, 修一
- 融, 健
Publication date
July 2009
DOI Publisher
Royal Society of Chemistry ISSN
1477-0520 Citation count (estimate)
50Abstract
Chiral nonracemic guanidines act as Bronsted bases to generate guanidinium enolates for the enantioselective electrophilic trifluoromethylation of β-keto esters by means of S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate (Umemoto reagent) with good enantioselectivity of 60-70% range. Despite the fact that the ees are still improvable, the model reported in this work could spark the imagination of chemists to design new chiral bases to improve the stereochemical outcome
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