Stereoselective C9 carbon-carbon couplings of quinine:: Synthesis and conformational analysis of new C2-symmetric dimers

被引：9

作者：

Boratynski, Przemyslaw J. ^{[1
]}

Turowska-Tyrk, Ilona ^{[2
]}

Skarzewski, Jacek ^{[1
]}

机构：

[1] Wroclaw Univ Technol, Dept Organ Chem, PL-50370 Wroclaw, Poland

[2] Wroclaw Univ Technol, Inst Phys & Theoret Chem, Fac Chem, PL-50370 Wroclaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 18期

关键词：

D O I：

10.1021/jo801205n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unexpected stereoselective direct dimerization Occurred when 9-quinine halide was treated with butyllithium. The reaction of either (9S)- or (9R)-chloroquinine gave the same C-2-symmetric dimer with 9R configuration (X-ray structure). A tentative mechanism involving radical recombination is discussed. This highly congested dimer forms two atropisomers, and their reversible interconversion was studied by NMR. Another C-2-symmetric (9S)-quinine dinner connected solely by carbon-carbon bonds was obtained by the stereoselective coupling of bis(arylbromomagnesium) derivative with (9S)-chloroquinine.

引用

页码：7357 / 7360

页数：4

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