Abstract
A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.
Original language | English |
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Pages (from-to) | 1171-1177 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 67 |
Issue number | 6 |
DOIs | |
Publication status | Published - 2011 Feb 11 |
Keywords
- Camphor
- Linker
- Michael addition
- Nitroolefins
- Organocatalysis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry