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Preparation of enantiomerically enriched α-hydroxy acid derivatives from α-alkoxyorganostannanes

✍ Scribed by Philip C.-M. Chan; J. Michael Chong

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
224 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Enantiomerically enriched

(9598%) a-alkoxy acids of defined absolute stereochemistry were prepared in good (83-99%) yields from a-alkoxyorganostannanes.

📜 SIMILAR VOLUMES

Enantioselective synthesis of α-hydroxy
Enantioselective synthesis of α-hydroxy carboxylic acids: Direct conversion of α-oxocarboxylic acids to enantiomerically enriched α-hydroxy carboxylic acids via neighboring group control
✍ Zhe Wang; Brittany La; Joseph M. Fortunak; Xian-Jun Meng; George W. Kabalka 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 183 KB

o~-Oxocarboxylic acids can be reduced to the corresponding ~-hydroxy carboxylic acids employing DIP-CI ~ as a reducing agent. The cz-carboxylic substituent exerts a remarkable neighboring group effect on the reduction. The reaction presumably proceeds in an intramolecular fashion through a "'rigid"