Novel chiral biheteroaromatic diphosphine oxides for lewis base activation of lewis acids in enantioselective allylation and epoxide opening

被引：39

作者：

Sirnonini, Valentina ^{[1
]}

Benaglia, Maurizio ^{[1
]}

Benincori, Tiziana ^{[2
]}

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 04期

关键词：

allylation; biheteroaromatic diphosphine oxides; chiral Lewis bases; organic catalysts;

D O I：

10.1002/adsc.200700564

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Enantiomerically pure biheteroaromatic diphosphine oxides were synthesised and tested as organocatalysts in two different reactions involving trichlorosilyl compounds. The allylation of aldehydes with allyl(trichloro)silane afforded homoallylic alcohols in fair to good yields and up to 95% ee. Preliminary experiments showed that this new class of metal-free catalysts was able also to promote the stilbene oxide opening by addition of tetrachlorosilane with enantioselectivity higher than 80%. The interesting results in terms of chemical and stereochemical efficiency open the way to further studies towards the development of new chiral heteroaromatic Lewis bases as efficient metal-free catalysts.

引用

页码：561 / 564

页数：4

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