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Organocatalytic Asymmetric C(sp 2 )−H Allylic Alkylation: Enantioselective Synthesis of Tetrasubstituted Allenoates
Author(s) -
Hu Yimin,
Shi Wangyu,
Zheng Bing,
Liao Jianning,
Wang Wei,
Wu Yongjun,
Guo Hongchao
Publication year - 2020
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.202009460
Subject(s) - stereocenter , enantioselective synthesis , tsuji–trost reaction , chirality (physics) , allylic rearrangement , chemistry , organocatalysis , alkylation , axial chirality , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , physics , chiral symmetry , nambu–jona lasinio model , quantum mechanics , quark
Abstract Herein we describe the first organocatalytic asymmetric C(sp 2 )−H allylation of racemic trisubstituted allenoates with Morita–Baylis–Hillman (MBH) carbonates to access axially chiral tetrasubstituted allenoates. Various trisubstituted allenoates and MBH carbonates were well tolerated under mild reaction conditions, providing novel chiral tetrasubstituted allenoates with adjacent axial chirality and tertiary carbon stereocenters in high yields with good to excellent diastereoselectivities and enantioselectivities.