Regio‐ and Enantioselective Copper‐Catalyzed 1, 4‐Conjugate Addition of Trimethylaluminium to Linear α, β, γ, δ‐Unsaturated Alkyl Ketones. Issue 15 (1st August 2016)

• Record Type: Journal Article
• Authors: Wu, Xiaoting; Xie, Fang; Ling, Zheng; Tang, Liang; Zhang, Wanbin
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 15(2016)
• Page Start: 2510
• Page End: 2518
• Publication Date: 2016-08-01
• Subjects: asymmetric catalysis -- 1, 4-conjugate addition reaction -- copper-catalyzed addition -- linear α, β, γ, δ-unsaturated alkyl ketones -- organoaluminium reagents; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600375
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A regio‐ and enantioselective copper‐catalyzed 1, 4‐conjugate addition of trimethylaluminium to linear δ‐aryl‐substituted α, β, γ, δ‐unsaturated alkyl ketones was developed. A series of γ, δ‐unsaturated alkyl ketones were obtained in good yields with high regio‐ and enantioselectivity (up to 88% ee and 96:4 dr ). Expansion of the reaction scope to substrates containing aromatic heterocycles also afforded good yields and enantioselectivities (up to 91% ee ) with very high regioselectivities, exclusively providing the single 1, 4‐products. Abstract :