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Tandem Thorpe Reaction/Palladium Catalyzed Asymmetric Allylic Alkylation: Access to Chiral β‐enaminonitriles with Excellent Enantioselectivity
Author(s) -
Bai DaChang,
Liu XiuYan,
Li Hao,
Ding ChangHua,
Hou XueLong
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601571
Subject(s) - carbanion , chemistry , tsuji–trost reaction , nitrile , catalysis , nucleophile , palladium , allylic rearrangement , alkylation , acetonitrile , reagent , tandem , combinatorial chemistry , medicinal chemistry , organic chemistry , composite material , materials science
A new type of nucleophile, a 3‐imino nitrile carbanion generated in situ by Thorpe reaction of acetonitrile with a base, was developed successfully and applied in a Pd‐catalyzed asymmetric allylic alkylation with mono‐substituted allyl reagents under Pd/SIOCPhox catalysis, affording β‐enaminonitrile products in high yields with excellent regio‐ and enantioselectivities.