Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates
✍ Scribed by Javier Adrio; Juan C. Carretero; Jose L. García Ruano; Luisa M. Martín Cabrejas
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- English
- Weight
- 580 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0957-4166
No coin nor oath required. For personal study only.
✦ Synopsis
Enantioselective synthesis of (+)-shikimic acid and (+)-5.epi-shikimic
acid by asymmetric Diels-Alder reaction of (S)-tx-sulfinylacrylates
📜 SIMILAR VOLUMES
Enantiospecific Synthesis of (-)-5-epi-Shikimic Acid and (-)-Shikimic Acid. -The key step in the synthesis of the title compounds (XI) and (XVI) is the intramolecular cycloaddition of the nitrones (V) and (XIV). -
The highly enantioselective Diels-Alder reaction between acryloyl oxazolidinone and furan, catalyzed by cationic bis(4-tert-butyloxazoline)Cu(II) complex 1, is presented. Though the reaction equilibrates rapidly at -20 °C, reaction at -78 °C permits isolation of the kinetic product mixture. The synt
Cationic Bis(oxazoline)Cu(II) Lewis Acid Catalysts. Enantioselective Furan Diels-Alder Reaction in the Synthesis of ent-Shikimic Acid. -In the synthesis of the title compound (IX) the key intermediate (III) is obtained under optimized conditions via an enantioselective Diels-Alder reaction. It is no
## Abstract The enantioselective synthesis of [5‐^2^H]‐5‐epi‐shikimic acid starting from commercially available L‐shikimic acid has been accomplished in this work. The introduction of the stable isotope was facilitated by an enzymic reduction of a ketone. An interesting stereospecific enolisation w