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A new system for catalytic enantioselective reduction of achiral ketones to chiral alcohols. Synthesis of chiral α-hydroxy acids

✍ Scribed by E.J Corey; Raman K Bakshi

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

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✦ Synopsis

The reduction of a variety of achiral ketones with catecholborane as stoichiometric reductant and 0.1 equiv of oxaxaborolidine 2 as catalyst in toluene at -78'C proceeds in > 95% yield and with enantioselectivities in the range 30: 1 to 9: 1, depending on substrate. This reduction procedure is especially advantageous for a$-enones, thereby providing chiral precursors for a great variety of compounds, for example, a-hydroxy acids.

📜 SIMILAR VOLUMES

Suitably designed chiral amino alcohols:
Suitably designed chiral amino alcohols: synthesis, resolution and application to the catalytic enantioselective reduction of aryl alkyl ketones
✍ I. Reiners; J. Martens 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 301 KB

The amino alcohol rac-1-(1,2,3,4-tetrahydroisoquinoline-1-yl)-cyclopentanol was resolved via its O,O'-dibenzoyl-tartaric acid salt. These enantiomeric amino alcohols were used in the enantioselective reduction of prochiral aryl alkyl ketones. The resulting secondary alcohols were obtained in high en