当前位置:
X-MOL 学术
›
J. Am. Chem. Soc.
›
论文详情
Our official English website, www.x-mol.net, welcomes your
feedback! (Note: you will need to create a separate account there.)
Direct Catalytic Asymmetric Addition of Allyl Cyanide to Ketones
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2009-03-11 , DOI: 10.1021/ja900001u
Ryo Yazaki 1 , Naoya Kumagai 1 , Masakatsu Shibasaki 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2009-03-11 , DOI: 10.1021/ja900001u
Ryo Yazaki 1 , Naoya Kumagai 1 , Masakatsu Shibasaki 1
Affiliation
A direct catalytic asymmetric addition of allyl cyanide to ketones with a bimetallic catalytic system comprising (R,R)-Ph-BPE/[Cu(CH(3)CN)(4)]ClO(4)/LiOAr is described. Exclusive gamma-addition of allyl cyanide was observed, affording optically enriched tertiary alcohols bearing Z-configured alpha,beta-unsaturated nitriles. The reaction proceeded under proton-transfer conditions, utilizing soft Lewis acid/hard Brønsted base bifunctional catalysis. The applicability of the reaction to aromatic, heteroaromatic, and aliphatic ketones demonstrates its wide substrate generality.
中文翻译:
烯丙基氰化物与酮的直接催化不对称加成
描述了使用包含 (R,R)-Ph-BPE/[Cu(CH(3)CN)(4)]ClO(4)/LiOAr 的双金属催化系统将烯丙基氰化物直接催化不对称加成到酮中。观察到烯丙基氰化物的独家伽马加成,提供带有 Z 构型 α,β-不饱和腈的光学富集叔醇。该反应在质子转移条件下进行,利用软路易斯酸/硬布朗斯台德碱双功能催化。该反应对芳香族、杂芳香族和脂肪族酮的适用性证明了其广泛的底物通用性。
更新日期:2009-03-11
中文翻译:
烯丙基氰化物与酮的直接催化不对称加成
描述了使用包含 (R,R)-Ph-BPE/[Cu(CH(3)CN)(4)]ClO(4)/LiOAr 的双金属催化系统将烯丙基氰化物直接催化不对称加成到酮中。观察到烯丙基氰化物的独家伽马加成,提供带有 Z 构型 α,β-不饱和腈的光学富集叔醇。该反应在质子转移条件下进行,利用软路易斯酸/硬布朗斯台德碱双功能催化。该反应对芳香族、杂芳香族和脂肪族酮的适用性证明了其广泛的底物通用性。