Asymmetric Synthesis of α-Trifluoromethylthio-β-Amino Acids under Phase Transfer Catalysis

被引：36

作者：

Capaccio, Vito ^{[2
]}

Sicignano, Marina ^{[1
]}

Rodriguez, Ricardo, I ^{[2
]}

Della Sala, Giorgio ^{[1
]}

Aleman, Jose ^{[2
]}

机构：

[1] Univ Salerno, Dipartimento Chim & Biol A Zambelli, Via Giovanni Paolo II 132, I-84084 Fisciano, SA, Italy

[2] Univ Autonoma Madrid, Organ Chem Dept, Modulo 1, E-28049 Madrid, Spain

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 01期

关键词：

PEPTIDE BUNDLES; ISOXAZOLIDIN-5-ONES; REAGENTS; DESIGN; DI;

D O I：

10.1021/acs.orglett.9b04195

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric alpha-trifluoromethylthiolation of 2-substituted isoxazolidin-5-ones was developed using Maruoka type N-spiro ammonium catalysts under phase-transfer conditions. The resulting products, containing a trifluoromethylthiolated quaternary chiral carbon, were obtained in moderate to good yields and up to 98:2 enantiomeric ratio. Moreover, the easy N-O bond cleavage provided access to undescribed alpha-trifluoromethylthio-beta(2,)(2)-amino acids, with promising applications in biochemistry and medicinal chemistry.

引用

页码：219 / 223

页数：5

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