Synthesis and analytical properties of (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid
✍ Scribed by Akio Ichikawa; Hiroshi Ono; Nobuyuki Harada
- Book ID
- 104359875
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 211 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
2-Methoxy-2-(9-phenanthryl)propionic acid was synthesized as a novel chiral resolving agent. The absolute configuration of (+)-2-methoxy-2-(9-phenanthryl)propionic acid was determined to be S by using X-ray structural analysis of the (1R,2S,5R)-menthyl ester. In the crystal, the methoxyl and carbonyl groups of the ester are in a syn-periplanar position. The syn-periplanar conformations of (1R,2S,5R)-menthyl esters were also observed by the NMR analyses in CDCl 3 . The utility of (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid was exemplified by the resolution of (±)-3-octanol.
📜 SIMILAR VOLUMES
## Abstract A practical synthesis of (2R)‐ and (2S)‐[2‐^3^H]‐propionic acid is described. The key steps in the synthesis are the reduction of [__formyl__‐^3^H]‐3‐methoxy‐4‐mesyloxybenzaldehyde with R‐ or S‐Alpine Borane to (7S)‐ and (7R)‐[7‐^3^H]‐3‐methoxy‐4‐mesyloxybenzyl alcohol and the use of th