Liao Fu-Min, Gao Xiao-Tong, Hu Xiao-Si, Xie Shi-Liang, Zhou Jian
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China; State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Chemical Engineering, East China Normal University, Shanghai 200062, China.
Sci Bull (Beijing). 2017 Nov 30;62(22):1504-1509. doi: 10.1016/j.scib.2017.10.016. Epub 2017 Nov 7.
We report a general and highly efficient Mukaiyama-aldol reaction of ketones and difluoroenoxysilanes. While the reaction of aryl ketones worked efficiently in the presence of Bi(OTf), that of aliphatic ketones required the use of Sc(OTf). In addition, Sc(OTf) was capable of achieving excellent 1,2-selectivity in the corresponding reaction of α,β-unsaturated ketones. This method provides a facile access to differently substituted β-hydroxy α,α-difluoro ketones, versatile synthons for difluomethylated tertiary alcohols.
我们报道了一种通用且高效的酮与二氟烯氧基硅烷的Mukaiyama-羟醛反应。虽然芳基酮的反应在Bi(OTf)存在下能有效进行，但脂肪族酮的反应则需要使用Sc(OTf)。此外，Sc(OTf)能够在α,β-不饱和酮的相应反应中实现优异的1,2-选择性。该方法为合成不同取代的β-羟基-α,α-二氟酮提供了一种简便途径，而β-羟基-α,α-二氟酮是用于二氟甲基化叔醇的通用合成子。
