Enantioselective Phase-Transfer Catalyzed α-Sulfanylation of Isoxazolidin-5-ones: An Entry to β2,2-Amino Acid Derivatives

被引：42

作者：

Cadart, Timothee ^{[1
]}

Berthonneau, Clement ^{[1
]}

Levacher, Vincent ^{[1
]}

Perrio, Stephane ^{[2
]}

Briere, Jean-Francois ^{[1
]}

机构：

[1] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA UMR 6014, F-76000 Rouen, France

[2] Normandie Univ, ENSICAEN, UNICAEN, CNRS,LCMT, F-14000 Caen, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 43期

关键词：

isoxazolidinone; phase-transfer catalysis; sulfanylation; synthetic methods; beta-amino acid; ASYMMETRIC-SYNTHESIS; BETA; BETA-DISUBSTITUTED NITROALKENES; MELDRUMS ACID; CONJUGATE ADDITION; MICHAEL REACTION; ORGANOCATALYSIS; PEPTIDOMIMETICS; STEREOCENTERS; CONSTRUCTION; PEPTIDES;

D O I：

10.1002/chem.201603910

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented enantioselective alpha-functionalization of C4-substituted N-alkoxycarbonyl isoxazolidin-5-ones, readily available platforms from Meldrum's acid derivatives, by N-sulfanylphthalimide (PhthSR) electrophiles was achieved upon an efficient phase-transfer catalytic approach, mediated by a commercial N-spiro quaternary ammonium catalyst. Two catalytic activities of the in situ formed R4N(+)Phth(-) species were highlighted, the phtalimidate being involved in the anion metathesis event and likely as a Bronsted base. This sequence offers a straightforward access to alpha,alpha-disubstituted isoxazolidinones, which turned out to be useful precursors of alpha-sulfanyl-beta(2,2)-amino acid derivatives.

引用

页码：15261 / 15264

页数：4

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