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Enantio‐ and Diastereoselective Synthesis of β ‐ Aryl ‐ β ‐ pyrazolyl α‐Amino Acid Esters via Copper‐Catalyzed Reaction of Azomethine Ylides with Benzylidenepyrazolones
Author(s) -
Gong YanChuan,
Wang Yue,
Li ErQing,
Cui Hao,
Duan Zheng
Publication year - 2019
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.201801137
Subject(s) - chemistry , stereocenter , aromatization , catalysis , stereoselectivity , aryl , copper , amino acid , reaction conditions , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , biochemistry , alkyl
A fully stereoselective synthesis of unnatural chiral β‐aryl‐β ‐ pyrazolyl α‐amino acid esters via copper‐catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1 H ‐pyrazol‐5‐ol was introduced by the aromatization of 3 H ‐pyrazol‐3‐one in the reaction. The transformation operated at room temperature and afforded β‐1 H ‐pyrazol‐5‐ol‐α‐amino esters in high yields with good to excellent levels of diastereo‐ and enantioselectivity.