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Silicon‐based Bulky Group−Tuned Parallel Kinetic Resolution in Copper‐Catalyzed 1,3‐Dipolar Additions
Author(s) -
Yuan Yang,
Zheng ZhanJiang,
Li Li,
Bai XingFeng,
Xu Zheng,
Cui YuMing,
Cao Jian,
Yang KeFang,
Xu LiWen
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800220
Subject(s) - stereocenter , chemistry , kinetic resolution , enantioselective synthesis , reactivity (psychology) , catalysis , conjugate , combinatorial chemistry , cycloaddition , cascade reaction , functional group , stereochemistry , tandem , carbon fibers , amino acid , 1,3 dipolar cycloaddition , organic chemistry , medicine , mathematical analysis , polymer , alternative medicine , mathematics , materials science , pathology , composite number , composite material , biochemistry
The development of new strategies or reaction processes that tease new reactivity of functional groups continues to spur synthetic chemists toward innovative solutions that access new compounds. Herein, we find that the silicon‐based bulky group enables a 1,3‐dipolar addition−initiated parallel kinetic resolution (PKR) to occur unexpectedly, leading to the highly enantioselective synthesis of two structurally different types of amino acid derivatives via chemodivergent [3+2] cycloaddition reactions and tandem conjugate addition‐elimination reaction respectively. The resulting and structurally divergent enantioenriched amino acid derivatives that contain four contiguous stereogenic centers and an all‐carbon quaternary center were obtained with up to 99% ee with >95:1 dr and good yields.