Organocatalytic Enantioselective Strecker Synthesis of α-Quaternary α-Trifluoromethyl Amino Acids

被引：92

作者：

Enders, Dieter ^{[1
]}

Gottfried, Katharina ^{[1
]}

Raabe, Gerhard ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 18期

关键词：

amino acids; organocatalysis; quaternary stereocenters; Strecker reaction; trifluoromethyl group; CATALYTIC ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; MICHAEL-ADDITION; RECENT PROGRESS; TMS-SAMP; NUCLEOPHILIC 1,2-ADDITION; ENZYMATIC RESOLUTION; PEPTIDE MODIFICATION; CHIRAL EQUIVALENT; FLUORINE;

D O I：

10.1002/adsc.201000666

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first organocatalytic enantioselective Strecker synthesis of alpha-quaternary alpha-trifluoromethylated amino acids has been developed. Employing Takemoto's thiourea catalyst the nucleophilic addition of trimethylsilyl cyanide to trifluoromethyl ketimines affords alpha-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.

引用

页码：3147 / 3152

页数：6

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