6‐Azabicyclo[3.2.1]octanes via Copper‐Catalyzed Enantioselective Alkene Carboamination. Issue 11 (25th June 2014)

• Record Type: Journal Article
• Authors: Casavant, Barbara J.; Hosseini, Azade S.; Chemler, Sherry R.
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 11/12(2014)
• Page Start: 2697
• Page End: 2702
• Publication Date: 2014-06-25
• 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.201400317
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Bridged bicyclic rings containing nitrogen heterocycles are important motifs in bioactive small organic molecules. An enantioselective copper‐catalyzed alkene carboamination reaction that creates bridged heterocycles is reported herein. Two new rings are formed in this alkene carboamination reaction where <italic>N</italic>‐sulfonyl‐2‐aryl‐4‐pentenamines are converted to 6‐azabicyclo[3.2.1]octanes using the complex [Ph‐Box‐Cu](OTf)₂ or related catalysts in the presence of manganeses dioxide (MnO₂) as stoichiometric oxidant in moderate to good yields and generally excellent enantioselectivities. Two new stereocenters are formed in the reaction, and the CC bond‐forming arene addition is a net CH functionalization.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh11pkdkzz" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>