Β‐Hydroxyamide‐Based Ligands and Their Use in the Enantioselective Borane Reduction of Prochiral Ketones. Issue 1 (6th November 2013)

• Record Type: Journal Article
• Authors: Azizoglu, Murat; Erdogan, Asli; Arslan, Nevin; Turgut, Yilmaz
• Is Part Of: Chirality. Volume 26:Issue 1(2014:Jan.)
• Page Start: 21
• Page End: 26
• Publication Date: 2013-11-06
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22254
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>ABSTRACT</title> <p>Hydroxyamide‐based ligands have occupied a considerable place in <named-content id="d664e1054" content-type="reactionType chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">asymmetric synthesis</named-content>. Here we report the synthesis of seven β‐hydroxyamide‐based ligands from the reaction of 2‐hydroxynicotinic acid with chiral amino alcohols and test their effect on the <named-content id="d664e1060" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselective</named-content> reduction of aromatic prochiral ketones with borane in tetrahydofuran (THF). They produce the corresponding secondary alcohols with up to 76% enantiomeric excess (<italic>ee</italic>) and good to excellent yields (86‐99%). <italic>Chirality 26:21–26, 2013</italic>. © 2013 Wiley Periodicals, Inc.</p> </abstract>