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Enantioselective Synthesis of Thiazole‐Derived α‐Perfluoroalkylated 5–7‐Membered Amines
Author(s) -
Voznesenskaia Natalia G.,
Shmatova Olga I.,
Ilyin Mikhail M.,
Ilyin Mikhail M.,
Nenajdenko Valentine G.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801845
Subject(s) - chemistry , enantioselective synthesis , thiazole , yield (engineering) , strecker amino acid synthesis , sulfide , organic chemistry , stereochemistry , medicinal chemistry , catalysis , materials science , metallurgy
Enantioselective synthesis of thiazole‐containing α‐perfluoroalkylated cyclic amines was elaborated. Organocatalytic Strecker reaction with 5–7 membered cyclic ketimines was used as a key step of sequence. The prepared chiral amino nitriles bearing CF 3 ‐ or C 2 F 5 ‐group in the alpha position were transformed into the corresponding chiral thioamides by the reaction with hydrogen sulfide. Subsequent reaction with alpha bromo‐ or chloro‐substituted carbonyls allowed obtaining perfluoroalkylated analogues of natural thiazole‐containing cyclic amines in high isolated yield and up to > 99 % ee .