The Use of Phosphite‐Type Ligands in the Ir‐Catalyzed Asymmetric Hydrogenation of Heterocyclic Compounds. Issue 1 (22nd November 2013)

• Record Type: Journal Article
• Authors: Lyubimov, Sergey E.; Ozolin, Dmitry V.; Ivanov, Pavel Yu; Melman, Artem; Velezheva, Valeriya S.; Davankov, Vadim A.
• Is Part Of: Chirality. Volume 26:Issue 1(2014:Jan.)
• Page Start: 56
• Page End: 60
• Publication Date: 2013-11-22
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22267
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>ABSTRACT</title> <p>A series of chiral phosphite‐type ligands was tested in asymmetric Ir‐catalyzed <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">hydrogenation</named-content> of quinolines and 2, 4, 5, 6‐tetrahydro‐1H‐pyrazino(3, 2, 1‐<italic>j</italic>, <italic>k</italic>)carbazole. <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Hydrogenation</named-content> of quinaldine hydrochloride provided superior <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselectivity</named-content> up to 65% <italic>ee</italic> compared to quinaldine free base. The ligands were tested for the first time in the asymmetric Ir‐Ircatalyzed <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">hydrogenation</named-content> of 2, 4, 5, 6‐tetrahydro‐1H‐pyrazino(3, 2, 1‐<italic>j</italic>, <italic>k</italic>)carbazole yielding the antidepressant drug, pirlindole. <italic>Chirality 26:56–60, 2013</italic>. © 2013 Wiley Periodicals, Inc.</p> </abstract>