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Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric S N 2′ Reaction
Author(s) -
Kuroda Yusuke,
Harada Shingo,
Oonishi Akinori,
Yamaoka Yousuke,
Yamada Kenichi,
Takasu Kiyosei
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201502831
Subject(s) - enantioselective synthesis , intramolecular force , tsuji–trost reaction , chemistry , catalysis , brønsted–lowry acid–base theory , alkylation , group (periodic table) , leaving group , organocatalysis , stereochemistry , allylic rearrangement , combinatorial chemistry , medicinal chemistry , organic chemistry
A Brønsted‐acid‐catalyzed intramolecular enantioselective S N 2′ reaction was developed utilizing trichloroacetimidate as a leaving group. The findings indicated that dual activation of the substrates is operative. This metal‐free allylic alkylation allows highly enantioselective access to 2‐vinylpyrrolidines bearing various substituents.