Abstract
The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 with various R groups (CH3, C5H11, C-11 H-23) is reported. The key step makes use of the Mannich reaction for attachment of a chiral diamine-line 2 across the cavity. Yields for this step are good to excellent. One of the bridged compounds exhibits modest activity (27% ee) as an enantioselective catalyst in the addition of diethylzinc to benzaldehyde.
Original language | English |
---|---|
Pages (from-to) | 412-414 |
Number of pages | 3 |
Journal | Synlett |
Volume | 3 |
DOIs | |
Publication status | Published - 2001 |
Keywords
- bridged resorcin[4]arene
- ACID
- ALKYLATION
- chiral resorcin[4]arene.
- CALIXARENES
- Mannich reaction
- RESORCARENES
- enantioselective catalyst
- RING
- C-2v-symmetric diamine chiral auxiliary
- CALIX<4>RESORCINARENE DERIVATIVES
- SELECTIVE DERIVATIZATION
- CLOSURE
- RESORCINOL
- ALDEHYDES