Synthesis of axially chiral C₁₀-BridgePHOS oxides and their use as organocatalysts in enantioselective allylations of aldehydes

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• 作者：Jianzhong Chen ; Delong Liu ; Dongyang Fan ; Yangang Liu ; Wanbin Zhang
• 关键词：Axial chirality ; C10-BridgePHOS oxide ; Organocatalyst ; Enantioselective allylation ; Chiral homoallylic alcohol
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：23 September, 2013
• 年：2013
• 卷：69
• 期：38
• 页码：8161-8168
• 全文大小：642 K

文摘

A series of C₁₀-BridgePHOS oxides possessing different substituted groups on the diphenyl phosphine system were synthesized and tested as organocatalysts in the allylation of aldehydes with allyltrichlorosilane, providing chiral homoallylic alcohols. These types of organocatalysts showed high catalytic activity and only 2 mol % catalyst loading was required to induce short reaction times. Under optimal reaction conditions, excellent product yields and up to 92 % ee were obtained for a variety of substrates.