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Chemoselective allylic addition of allyltrichlorosilane to α-oxocarboxylic acids: synthesis of tertiary α-hydroxy carboxylic acids

✍ Scribed by Zhe Wang; Guoyou Xu; Dengjin Wang; Michael E. Pierce; Pat N. Confalone

Book ID
108379807
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
126 KB
Volume
41
Category
Article
ISSN
0040-4039

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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"