Enantioselective Hydroalkynylation of Non‐Polar Carbon‐Carbon Double Bonds: Iridium‐Catalyzed Asymmetric Addition Reaction of Terminal Alkyne CH Bonds to Substituted Norbornadienes. Issue 10 (6th July 2015)

• Record Type: Journal Article
• Authors: Yang, Qingjing; Choy, Pui Ying; Fan, Baomin; Kwong, Fuk Yee
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 10(2015)
• Page Start: 2345
• Page End: 2350
• Publication Date: 2015-07-06
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500465
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>This update describes the enantioselective addition of the terminal alkynyl CH bond across a non‐polar CC double bond. Sterically congested substrates are often challenging in this type of reaction as these alkenyl substrates exhibit poor substrate‐metal center coordination, and thus poor stereo‐induction would result. The successful enantioselective hydroalkynylation of this type of system has sporadically been reported. We herein describe our progress for the example of vinyl‐substituted norbornadiene derivatives. With the aid of an iridium complex in combination with the chiral SYNPHOS ligand, the addition products could be obtained smoothly with excellent enantioselectivities (up to 99% <italic>ee</italic>). In particular, the first examples of an acetylenic CH bond adding across azanorbornadienes are also disclosed.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgj22cj59z9" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>