✦ LIBER ✦

Enantioselective synthesis of α-hydroxy carboxylic acids: Direct conversion of α-oxocarboxylic acids to enantiomerically enriched α-hydroxy carboxylic acids via neighboring group control

✍ Scribed by Zhe Wang; Brittany La; Joseph M. Fortunak; Xian-Jun Meng; George W. Kabalka

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 183 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01162-9

No coin nor oath required. For personal study only.

✦ Synopsis

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" bicyclic transition state assembly, which produces enantioselectivities approaching 99%.

📜 SIMILAR VOLUMES

ChemInform Abstract: Enantioselective Sy

ChemInform Abstract: Enantioselective Synthesis of α-Hydroxy Carboxylic Acids: Direct Conversion of α-Oxocarboxylic Acids to Enantiomerically Enriched α-Hydroxy Carboxylic Acids via Neighboring Group Control.

✍ Z. WANG; B. LA; J. M. FORTUNAK; X.-J MENG; G. W. KABALKA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

ChemInform Abstract: Enantioselective Sy

ChemInform Abstract: Enantioselective Synthesis of β-Hydroxy Carboxylic Acids: Direct Conversion of β-Oxocarboxylic Acids to Enantiomerically Enriched β-Hydroxy Carboxylic Acids via Neighboring Group Control.

✍ Zhe Wang; Chunlin Zhao; Michael E. Pierce; Joseph M. Fortunak 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

ChemInform Abstract: Chemoselective Ally

ChemInform Abstract: Chemoselective Allylic Addition of Allyltrichlorosilane to α-Oxocarboxylic Acids: Synthesis of Tertiary α-Hydroxy Carboxylic Acids.

✍ Zhe Wang; Guoyou Xu; Dengjin Wang; Michael E. Pierce; Pat N. Confalone 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 1 views

Synthesis of non-natural α-hydroxy and α

Synthesis of non-natural α-hydroxy and α-thio carboxylic acids using hexafluoroacetone as protecting group

✍ E. Windeisen; E. Heistracher; K. Burger 📂 Article 📅 1991 🏛 Elsevier Science 🌐 English ⚖ 37 KB

Synthesis of α-Hydroxy Carboxylic Acids

Synthesis of α-Hydroxy Carboxylic Acids via a Nickel(II)- Catalyzed Hydrogen Transfer Process

✍ Guo Tang; Chien-Hong Cheng 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 187 KB 👁 1 views

Asymmetric synthesis of α-hydroxy carbox

Asymmetric synthesis of α-hydroxy carboxylic acids: direct oxidation of chiral amide enolates using 2-sulfonyloxaziridines

✍ Franklin A. Davis; Lal C. Vishwakarma 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 237 KB

The direct oxidation of chiralamide enolates to optically active mandelic acidusingzsulfonyloxaziridine