Functionalization of [2.2]Paracyclophanes via a Reductive Sulfanylation Reaction

被引：7

作者：

Deschamps, Damien ^{[1
]}

Lohier, Jean-Francois ^{[1
]}

Richards, Christopher J. ^{[2
]}

Gaumont, Annie-Claude ^{[1
]}

Perrio, Stephane ^{[1
]}

机构：

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

[2] Univ East Anglia, Sch Chem, Norwich NR4 7TJ, Norfolk, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期

关键词：

ORGANOCATALYZED 3+2 ANNULATION; ENANTIOMERICALLY PURE; KINETIC RESOLUTION; LAYERED COMPOUNDS; ALLENYL SULFONES; PARACYCLOPHANES; SULFIDES; PLANAR; EFFICIENT; BRIDGES;

D O I：

10.1021/acs.joc.0c02235

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expeditious route to planar chiral sulfur-based scaffolds has been achieved in two operational steps from cheap and commercial [2.2]paracyclophane hydrocarbon. The sulfur atom was introduced in a specific benzylic position of the [2.2]paracyclophane according to a reductive sulfanylation reaction, which proceeds under two complementary reaction conditions with either the BF3 center dot OEt2/Et3SiH or TFA/BH3 center dot THF combinations. The study was completed by the development of a highly efficient resolution approach by HPLC.

引用

页码：507 / 514

页数：8

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