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Chiral Borate Esters in Asymmetric Synthesis. Part 5. Asymmetric Reduction of Oxime Ethers Promoted by Chiral Spiroborate Esters with an O3BN Framework.

✍ Scribed by Yunbo Chu; Zixing Shan; Dejun Liu; Nannan Sun


Publisher
John Wiley and Sons
Year
2006
Weight
22 KB
Volume
37
Category
Article
ISSN
0931-7597

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✦ Synopsis


Abstract

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## Abstract The first asymmetric reaction catalyzed by chiral spiroborated esters with an O~3~BN framework was reported. In the presence of 0.1 equivalent of (__R,S__)‐1 or (__S,S__)‐1, acetophenone was reduced by 0.6 equivalent of borne in THF at 0–5 Β°C for 2 h to give (R)‐1‐phenylethanol of up to

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## Abstract Asymmetric catalytic activity of the chiral spiroborate esters **1**–**9** with a O~3~BN framework (see __Fig.β€…1__) toward borane reduction of prochiral ketones was examined. In the presence of 0.1β€…equiv. of a chiral spiroborate ester, prochiral ketones were reduced by 0.6β€…equiv. of bor