Asymmetric Organocatalytic Cascade Michael/Hemiketalization/Retro‐Aldol Reaction of 2‐[(E)‐2‐Nitrovinyl]phenols with 2, 4‐Dioxo‐4‐arylbutanoates: A Convenient Access to Chiral α‐Keto Esters. Issue 13 (28th August 2013)

• Record Type: Journal Article
• Authors: Liu, Yunting; Wang, Youming; Song, Haibin; Zhou, Zhenghong; Tang, Chuchi
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 13(2013)
• Page Start: 2544
• Page End: 2549
• Publication Date: 2013-08-28
• 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.201300552
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>An unprecedented organocatalytic enantioselective cascade Michael/hemiketalization/retro‐aldol reaction of 2‐[(<italic>E</italic>)‐2‐nitrovinyl]phenols and 2, 4‐dioxo‐4‐arylbutanoates is described. With a bifunctional squaramide catalyst incorporating (1<italic>R</italic>, 2<italic>R</italic>)‐1, 2‐diphenylethane‐1, 2‐diamine, the reactions afford products in 75–99% yields with 80–98% <italic>ee</italic>. This process provides an enantioselective pathway for the synthesis of chiral α‐keto esters, precursors of 3‐arylproline derivatives, δ‐amino α‐keto acids or cyclic α‐keto lactams.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg3h7zqxff" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>