Construction of Quaternary Stereogenic Carbon Centers through Copper‐Catalyzed Enantioselective Allylic Alkylation of Azoles. Issue 15 (9th March 2016)

• Record Type: Journal Article
• Authors: Ohmiya, Hirohisa; Zhang, Heng; Shibata, Saori; Harada, Ayumi; Sawamura, Masaya
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 15(2016)
• Page Start: 4777
• Page End: 4780
• Publication Date: 2016-03-09
• Subjects: allylic compounds -- asymmetric catalysis -- carbenes -- copper -- heterocycles; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201600619
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Copper‐catalyzed enantioselective allylic alkylation of azoles with γ, γ‐disubstituted primary allylic phosphates was achieved using a new chiral N‐heterocyclic carbene ligand bearing a naphtholic hydroxy group. This reaction occurred with excellent branch regioselectivity and high enantioselectivity, thus forming a controlled all‐carbon quaternary stereogenic center at the position α to the heteroaromatic ring. Abstract : Branch out : The title reaction proceeds with γ, γ‐disubstituted primary allylic phosphates and a new chiral N‐heterocyclic carbene ligand bearing a naphtholic hydroxy group. The reaction occurs with excellent branch regioselectivity and high enantioselectivity, thus forming a controlled all‐carbon quaternary stereogenic center at the position α to the heteroaromatic ring.