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Borane-mediated asymmetric reduction of acetophenone by enantiopure aminonaphthols and aminoalcohols as catalytic source

✍ Scribed by Cristina Cimarelli; Davide Fratoni; Gianni Palmieri

Book ID: 102073643
Publisher: John Wiley and Sons
Year: 2009
Tongue: English
Weight: 294 KB
Volume: 22
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.20812

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✦ Synopsis

Abstract

Practical, cheap, and stereoselective synthetic methods were applied to the preparation of novel 1‐(aminoalkyl)naphthol and γ‐aminoalcohol tridentate ligands. The ligands obtained were conveniently applied with good results as catalytic sources in the borane‐mediated enantioselective reduction of acetophenone with borane dimethylsulfide. Conformational analysis through molecular modeling allows the rationalization of observed stereochemical outcomes. Chirality 2010. © 2009 Wiley‐Liss, Inc.

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