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

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67 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7030-7038
Number of pages9
JournalChemistry - A European Journal
Volume16
Issue number23
DOIs
Publication statusPublished - 2010 Jun 18

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Keywords

  • Camphor
  • Citronellal
  • Michael addition
  • Nitroalkenes
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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