𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Monobenzylether of (R,R)-1,2-diphenylethane-1,2-diol as chiral auxiliary in the diastereoselective reduction of α-ketoesters

✍ Scribed by Stefano Superchi; Michela Contursi; Carlo Rosini

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
394 KB
Volume
54
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis

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 of 4a.

📜 SIMILAR VOLUMES

The stereoselective conversion of 2-alke
The stereoselective conversion of 2-alkenyl alcohols to (R)- or (S)-alkane-1,2-diols using D-glucose as a chiral auxiliary
✍ Gang Huang; Rawle I. Hollingsworth 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 254 KB

The stereoselective addition of the 2-hydroxyl group of glucose to the mercurated vinyl group of 2-alkenyl glycosides followed by hydride reduction and removal of the saccharide fragment was used to prepare enantiomerically pure 1,2-dihydroxy alkanes. Diols of (R) or (S) configuration can be synthes