Chiral Phosphoric Acid‐Catalyzed Enantioselective Aza‐Friedel–Crafts Alkylation of Indoles with γ‐Hydroxy‐γ‐lactams. Issue 5 (15th March 2013)

• Record Type: Journal Article
• Authors: Courant, Thibaut; Kumarn, Sirirat; He, Long; Retailleau, Pascal; Masson, Géraldine
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 5(2013)
• Page Start: 836
• Page End: 840
• Publication Date: 2013-03-15
• 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.201201008
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>An enantioselective aza‐Friedel–Crafts reaction of indoles with γ‐hydroxy‐γ‐lactams using a chiral phosphoric acid catalyst is reported. The approach described herein provides an efficient access to 5‐indolylpyrrolidinones in good to quantitative yields and excellent enantioselectivities (up to &gt;99% <italic>ee</italic>). The results suggest that the reaction may proceed <italic>via N</italic>‐acyliminium intermediates associated with the chiral phosphoric acid anion.</p> </abstract>