Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to β-nitroalkenes

Ying Fang Ting, Chihliang Chang, Raju Jannapu Reddy, Dhananjay R. Magar, Kwunmin Chen*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

70 引文 斯高帕斯(Scopus)

摘要

Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted aldehydes to β-nitroalkenes. When this asymmetric transformation was cata-lyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diaste-reomeric ratio (d.r.) and 99% enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.

原文英語
頁(從 - 到)7030-7038
頁數9
期刊Chemistry - A European Journal
16
發行號23
DOIs
出版狀態已發佈 - 2010 六月 18

ASJC Scopus subject areas

  • 催化
  • 有機化學

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