Rhodium-catalyzed asymmetric addition of arylboronic acids to β-nitroolefins: Formal synthesis of (S)-SKF 38393

Kung Chih Huang, Balraj Gopula, Ting Shen Kuo, Chien Wei Chiang, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

43 引文 斯高帕斯(Scopus)

摘要

An efficient enantioselective addition of an array of arylboronic acids to various β-nitrostyrenes catalyzed by a novel and reactive rhodium-diene catalyst (S/C up to 1000) was developed, providing β,β- diarylnitroethanes in good to high yields (62-99%) with excellent enantioselectivities (85-97% ee). The method was extended to 2-heteroarylnitroolefins and 2-alkylnitroolefins similarly providing the desired products with high enantioselectivities and yields. The usefulness of this method was demonstrated in the formal synthesis of the enantiomer of the dopamine receptor agonist and antagonist, SKF 38393.

原文英語
頁(從 - 到)5730-5733
頁數4
期刊Organic Letters
15
發行號22
DOIs
出版狀態已發佈 - 2013 十一月 15

ASJC Scopus subject areas

  • 生物化學
  • 物理與理論化學
  • 有機化學

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