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Palladium‐Catalyzed Stereospecific Allylation of Nitroacetates with Enantioenriched Primary Allylic Amines
Author(s) -
Xu JingKun,
Wang Yong,
Gu Yonghong,
Tian ShiKai
Publication year - 2016
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.201600059
Subject(s) - chemistry , allylic rearrangement , stereospecificity , palladium , decarboxylation , catalysis , optically active , nitro , organic chemistry , primary (astronomy) , combinatorial chemistry , walden inversion , alkyl , physics , astronomy
An unprecedented stereospecific allylation reaction of nitroacetates with enantioenriched primary allylic amines has been developed. A range of nitroacetates smoothly underwent allylation with enantioenriched primary allylic amines in the presence of a palladium catalyst and boric acid followed by one‐pot decarboxylation to afford structurally diverse homoallylic nitro compounds in good to excellent yields with excellent retention of configuration. On the other hand, the allylation followed by denitronation provided a facile synthetic route to optically active β‐chiral γ,δ‐unsaturated esters.