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Synthesis of N-squaramidoacids and their application in asymmetric borane reduction of prochiral ketones

✍ Scribed by Ji Zhang; Lei-Lei Li; Hai-Hua Zou; Jun-Jun Chen; Kai-Bei Yu; Ru-Gang Xie

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
427 KB
Volume
22
Category
Article
ISSN
0256-7660

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✦ Synopsis

Abstract

A series of novel N‐squaramidoacid ligands were prepared conveniently. Without converting to corresponding amino alcohols, these ligands could be used in asymmetric borane reduction of prochiral aromatic ketones to give secondary alcohols in good to excellent enantiomeric excesses. The results showed that N‐squaramidoacids are more efficient ligands than N‐sulfonyl amino acids. N‐Squaryl proline was proved to be an excellent ligand in this catalytic asymmetric process.

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