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Enantioselective synthesis of ( R )‐Cinacalcet via cobalt‐catalysed asymmetric Negishi cross‐coupling
Author(s) -
Sun Xiao,
Wang Xueyang,
Liu Feipeng,
Gao Zidong,
Bian Qinghua,
Wang Min,
Zhong Jiangchun
Publication year - 2019
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23085
Subject(s) - chemistry , enantioselective synthesis , negishi coupling , cinacalcet , recrystallization (geology) , reagent , amine gas treating , cobalt , amide , enantiomer , enantiomeric excess , combinatorial chemistry , organic chemistry , catalysis , parathyroid hormone , paleontology , secondary hyperparathyroidism , biology , calcium
A novel enantioselective synthesis of ( R )‐cinacalcet with 99% enantiomeric excesses (ee) has been achieved. The main strategies of the approach include a gram‐scale cobalt‐catalysed asymmetric cross‐coupling of racemic ester with arylzinc reagent, Hoffman‐type rearrangement of acidamide, the amidation of chiral amine, and improving the ee of chiral amide from 87% to 99% via recrystallization.
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