Gold( I)-Catalyzed Enantioselective Desymmetrization of 1,3-Diols through Intramolecular Hydroalkoxylation of Allenes

被引：57
|
作者：
Zi, Weiwei [1 ]
Toste, F. Dean [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 48期
关键词：
allenes; desymmetrization; enantioselective synthesis; gold; hydroalkoxylation; TRANSITION-METAL CATALYSIS; ACYL TRANSFER; HYDROAMINATION; ALCOHOLS; BROMOETHERIFICATION; HYDROARYLATION; ALLYLATION; COMPLEXES; LIGANDS; ALKENES;
D O I：
10.1002/anie.201508331
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A gold(I)-catalyzed enantioselective desymmetrization of 1,3-diols was achieved by intramolecular hydroalkoxylation of allenes. The catalyst system 3-F-dppe(AuCl)(2)/(R)-C-8- TRIPAg proved to be specifically efficient to promote the desymmetrizing cyclization of 2-aryl-1,3-diols, which have proven challenging substrates in previous reports. Multisubstituted tetrahydrofurans were prepared in good yield with good enantioselectivity and diastereoselectivity by this method.
引用
收藏
页码：14447 / 14451
页数：5
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