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Diastereoselective reduction of α-keto esters bearing chiro-inositol derivatives as chiral auxiliaries

✍ Scribed by Takahiko Akiyama; Hiroyuki Nishimoto; Shoichiro Ozaki

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
259 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reduction of a-keto esters derived from (IL)-1,2;5,6-biscyclohexylidene-3-terrbutyldimethysilyl-chiro -inositol with Selectride@ proceeded with high diastereoselectivity to afford the corresponding a-hydroxy esters. Addition of l&Crown-6 led to dramatic changeover in diastereofacial selectivity.

Chira] a-hydroxy acid derivatives are important and versatile synthetic intermediates for the construction of

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Monobenzylether of (R,R)-1,2-diphenylethane-1,2-diol as chiral auxiliary in the diastereoselective reduction of α-ketoesters
✍ Stefano Superchi; Michela Contursi; Carlo Rosini 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 394 KB

The 0t-ketoester 4a, prepared in 3 steps from (R,R)-l,2-dipbenylethane-l,2-diol can be reduced with several agents providing the corresponding ¢t-hydroxyester 5 with diastereoselectivities up to 56%. This selectivity has been interpreted as due to earbonyl face-shielding by the stacked OCH2Ph moiety