Expeditious Synthesis of Enantioenriched Tetrahydropyrans via Chemoselective C-N bond Cleavage of Aza-Oxa-Bicyclo[3.2.1]Octanes

被引：5

作者：

D'Elia, Cecilia Sasso ^{[1
]}

Goudedranche, Sebastien ^{[1
]}

Constantieux, Thierry ^{[1
]}

Bella, Marco ^{[2
]}

Bonne, Damien ^{[1
]}

Rodriguez, Jean ^{[1
]}

机构：

[1] Aix Marseille Univ, CNRS, Cent Marseille, iSm2, Marseille, France

[2] Sapienza Univ Roma, Dipartimento Chim, Piazzale Aldo Moro 5, I-00185 Rome, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 20期

关键词：

Tetrahydropyrans; Azepanes; Organocatalysis; Multiple bond-forming transformations; Oxocarbenium ions; DOMINO METATHESIS; FUNCTIONALIZED TETRAHYDROPYRANS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; STRATEGIES; RINGS;

D O I：

10.1002/adsc.201700735

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A rapid synthesis of enantioenriched 2,3,4-trisubstituted tetrahydropyrans in good yields and stereoselectivities is reported. The first step is a domino organocatalytic reaction between ambident electrophilic and 1,4-bis-nucleophilic 1,2-ketoamides and 1,3-bis-electrophilic enals, leading to aza-oxa-bicyclo[3.2.1]octane. Then, the TiCl4/Et3SiH system ensures a chemoselective cleavage of the C-N bond and affords the desired trisubstituted tetrahydropyran in good yield and with conservation of the precursors optical purity. This final synthetic operation includes two consecutive oxocarbenium ion formation and reductions.

引用

页码：3638 / 3641

页数：4

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