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Palladium‐Catalyzed Allylic Alkylation of Aldimine Esters with Vinyl‐Cyclopropanes to Yield α,α‐Disubstituted α‐Amino Acid Derivatives
Author(s) -
Wang Jiahua,
Dai Zonghao,
Xiong Cheng,
Zhu Jin,
Lu Jinrong,
Zhou Qingfa
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901031
Subject(s) - chemistry , aldimine , tsuji–trost reaction , allylic rearrangement , palladium , alkylation , stereoselectivity , catalysis , enantioselective synthesis , organic chemistry , phosphine , yield (engineering) , diethylzinc , ligand (biochemistry) , combinatorial chemistry , biochemistry , materials science , receptor , metallurgy
Abstract A synthetically useful approach for the synthesis of functionalized α, α‐disubstituted α‐amino acid derivatives via palladium‐catalyzed 1,7 addition of readily available aldimine esters to vinylcyclopropanes is reported. This methodology was operated under mild conditions, affording α‐allylic α‐amino esters in good to excellent yields and excellent regio‐ and stereoselectivity. This transformation displays broad functional‐group tolerance and enantioselective allylic alkylation has also been realized using a chiral phosphine ligand to provide the desired product.