Premium
Organocatalytic Enantioselective Strecker Synthesis of α‐Quaternary α‐Trifluoromethyl Amino Acids
Author(s) -
Enders Dieter,
Gottfried Katharina,
Raabe Gerhard
Publication year - 2010
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.201000666
Subject(s) - chemistry , enantioselective synthesis , enantiopure drug , strecker amino acid synthesis , trifluoromethyl , trimethylsilyl cyanide , organic chemistry , organocatalysis , thiourea , nucleophile , amino acid , hydrolysis , cyanide , recrystallization (geology) , catalysis , biochemistry , paleontology , alkyl , biology
The first organocatalytic enantioselective Strecker synthesis of α‐quaternary α‐trifluoromethylated amino acids has been developed. Employing Takemoto’s thiourea catalyst the nucleophilic addition of trimethylsilyl cyanide to trifluoromethyl ketimines affords α‐amino nitriles in good to excellent yields (50–99%) and very good enantioselectivities ( ee =83–95%). The enantiopure amino nitriles can be obtained by recrystallization. Deprotection and hydrolysis leads to the title amino acids.