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Synergistic Kinetic Resolution and Asymmetric Propargyl Claisen Rearrangement for the Synthesis of Chiral Allenes
Author(s) -
Liu Yangbin,
Liu Xiaohua,
Hu Haipeng,
Guo Jing,
Xia Yong,
Lin Lili,
Feng Xiaoming
Publication year - 2016
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.201511776
Subject(s) - allene , propargyl , stereocenter , claisen rearrangement , kinetic resolution , chirality (physics) , chemistry , carroll rearrangement , stereochemistry , axial chirality , enantioselective synthesis , organic chemistry , physics , catalysis , chiral symmetry breaking , symmetry breaking , particle physics , nambu–jona lasinio model
The asymmetric propargyl Claisen rearrangement provides a convenient entry to chiral allene motifs. Herein, we describe the development of a kinetic resolution and asymmetric rearrangement of racemic propargyl vinyl ethers. This transformation afforded chiral allene products along with the enantiomerically enriched substrate in good yields with excellent diastereo‐ and enantioselectivity. The complete chirality transfer and facially selective rearrangement enabled the simultaneous construction of an axially chiral allenic unit and a quaternary carbon stereocenter.