A general and efficient Lewis acid catalysed Mukaiyama-aldol reaction of difluoroenoxysilanes and ketones

Fu-Min Liao; Xiao-Tong Gao; Xiao-Si Hu; Shi-Liang Xie; Jian Zhou

doi:10.1016/j.scib.2017.10.016

A general and efficient Lewis acid catalysed Mukaiyama-aldol reaction of difluoroenoxysilanes and ketones

Sci Bull (Beijing). 2017 Nov 30;62(22):1504-1509. doi: 10.1016/j.scib.2017.10.016. Epub 2017 Nov 7.

Authors

Fu-Min Liao¹, Xiao-Tong Gao¹, Xiao-Si Hu¹, Shi-Liang Xie¹, Jian Zhou²

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
² 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. Electronic address: jzhou@chem.ecnu.edu.cn.

PMID: 36659427
DOI: 10.1016/j.scib.2017.10.016

Abstract

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)₃, that of aliphatic ketones required the use of Sc(OTf)₃. In addition, Sc(OTf)₃ 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.

Keywords: Difluoroenoxysilanes; Ketones; Lewis acid catalysed; Mukaiyama-aldol reaction; β-Hydroxy α,α-difluoro ketones.