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Enantioselective Control of Both Helical and Axial Stereogenic Elements though an Organocatalytic Approach
Author(s) -
Jia Shiqi,
Li Shan,
Liu Yidong,
Qin Wenling,
Yan Hailong
Publication year - 2019
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.201909214
Subject(s) - stereocenter , enantioselective synthesis , stereochemistry , kinetic resolution , organocatalysis , chemistry , helix (gastropod) , catalysis , organic chemistry , biology , ecology , snail
A highly diastereo‐ and enantio‐selective method for the asymmetric synthesis of molecules containing helicenes and stereogenic axes was developed based on organocatalysis. Various compounds bearing both helical and axial stereogenic elements were obtained in excellent enantioselectivities. The mechanism study revealed that the reaction proceeded through two stages: 1) The first cyclization produces a reaction intermediate containing a stereogenic axis. 2) The dynamic kinetic resolution of helix reaction intermediate following with cyclization generates a helix and another stereogenic axis.