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 language | English |
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Pages (from-to) | 7030-7038 |
Number of pages | 9 |
Journal | Chemistry - A European Journal |
Volume | 16 |
Issue number | 23 |
DOIs | |
Publication status | Published - 2010 Jun 18 |
Keywords
- Camphor
- Citronellal
- Michael addition
- Nitroalkenes
- Organocatalysis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Organic Chemistry