Palladium-Catalyzed Asymmetric Allylic Alkylation of Azlactones: An Efficient Access to Unsaturated Trifluoromethylated α-Amino Acid Derivatives Possessing α-Quaternary Stereogenic Centers

Shuaibo Zhang; Luyang Sun; Dong Li; Jinfeng Zhao; Jingping Qu; Yuhan Zhou

doi:10.1055/a-2360-8289

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(20): 3220-3232
DOI: 10.1055/a-2360-8289

paper

Palladium-Catalyzed Asymmetric Allylic Alkylation of Azlactones: An Efficient Access to Unsaturated Trifluoromethylated α-Amino Acid Derivatives Possessing α-Quaternary Stereogenic Centers

Shuaibo Zhang

^aState Key Laboratory of Fine Chemicals, Department of Pharmaceutical Sciences, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Luyang Sun

^bState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Dong Li

^aState Key Laboratory of Fine Chemicals, Department of Pharmaceutical Sciences, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Jinfeng Zhao

^cInstrumental Analysis Center, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Jingping Qu

^bState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Yuhan Zhou ∗

^aState Key Laboratory of Fine Chemicals, Department of Pharmaceutical Sciences, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

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Abstract

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Abstract

A new strategy for the asymmetric allylic alkylation of azlactones with α-(trifluoromethyl)allyl acetates catalyzed by Pd(OAc)₂/(R)-BINAP is designed and developed, providing access to unsaturated α-quaternary α-amino acid derivatives bearing a trifluoromethyl group and contiguous quaternary and tertiary stereogenic centers. The products are obtained in good yields with exclusive regioselectivity and excellent stereoselective control under relatively mild reaction conditions. A scale-up experiment shows no loss of reactivity or stereoselectivity. The synthetic utility of the current strategy is demonstrated through transformations of a representative product to afford several potentially bioactive species.

Key words

palladium catalysis - trifluoromethyl alkylation - asymmetric catalysis - azlactones - α-(trifluoromethyl)allyl acetates

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