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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502831
Subject(s) - enantioselective synthesis , intramolecular force , chemistry , tsuji–trost reaction , catalysis , organocatalysis , brønsted–lowry acid–base theory , group (periodic table) , alkylation , stereochemistry , leaving group , medicinal chemistry , combinatorial 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.