Pyrrolidine-based amino alcohols: novel ligands for the enantioselective alkylation of benzaldehyde
A series of easily obtained pyrrolidine-based [beta]-amino alcohols derived from tartaric acid and primary amines was synthesized and used as chiral ligands in the enantioselective alkylation of benzaldehyde. Using diethylzinc, 1-phenyl-1-propanol was obtained with enantiomeric excesses of up to 80%...
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| Other Authors: | , , , , , , |
| Format: | article |
| Language: | eng |
| Published: |
2003
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| Subjects: | |
| Online Access: | http://hdl.handle.net/10316/5168 |
| Country: | Portugal |
| Oai: | oai:estudogeral.sib.uc.pt:10316/5168 |
| Summary: | A series of easily obtained pyrrolidine-based [beta]-amino alcohols derived from tartaric acid and primary amines was synthesized and used as chiral ligands in the enantioselective alkylation of benzaldehyde. Using diethylzinc, 1-phenyl-1-propanol was obtained with enantiomeric excesses of up to 80% when (3S,4S)-N-(1-naphthylmethyl)-3,4-dihydroxypyrrolidine was used. The nature of the N-substituent on the ligand, as well as the reaction temperature proved to significantly influence reaction product distribution as well as the enantiomeric excess of the chiral alcohol. |
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