Enantioselective Haloetherification by Asymmetric Opening of meso-Halonium Ions

被引:151
作者
Hennecke, Ulrich [1 ]
Mueller, Christian H. [1 ]
Froehlich, Roland [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
BRONSTED ACID; HALOCYCLIZATION; BROMOLACTONIZATION; CATALYSIS; METAL; IODOCYCLIZATION; THIIRANIUM; COMPLEXES; BROMONIUM; SALTS;
D O I
10.1021/ol1028805
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.
引用
收藏
页码:860 / 863
页数:4
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