Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters

Jin-Sheng Yu; Fu-Min Liao; Wei-Ming Gao; Kui Liao; Run-Lin Zuo; Jian Zhou

doi:10.1002/anie.201501747

Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters

Angew Chem Int Ed Engl. 2015 Jun 15;54(25):7381-5. doi: 10.1002/anie.201501747. Epub 2015 May 7.

Authors

Jin-Sheng Yu¹, Fu-Min Liao¹, Wei-Ming Gao¹, Kui Liao¹, Run-Lin Zuo², Jian Zhou^{3

4}

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China).
² No 15 class of Grade 2012, Luzhou High School, 33 Zhongshan Road, Luzhou 646000 (China).
³ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China). jzhou@chem.ecnu.edu.cn.
⁴ State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (P.R. China). jzhou@chem.ecnu.edu.cn.

PMID: 25950511
DOI: 10.1002/anie.201501747

Abstract

A chiral secondary amine phosphoramide was developed and identified as a powerful catalyst for the Mukaiyama-Michael addition of fluorinated enol silyl ethers to tetrasubstituted olefins. The resulting products are obtained with high enantioselectivities and contain a quaternary carbon stereocenter bearing either a difluoroalkyl or monofluoroalkyl group.

Keywords: amines; asymmetric catalysis; chirality; fluorine; organocatalysis.