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

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...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-06, Vol.54 (25), p.7381-7385
Main Authors: Yu, Jin-Sheng, Liao, Fu-Min, Gao, Wei-Ming, Liao, Kui, Zuo, Run-Lin, Zhou, Jian
Format: Article
Language:English
Subjects:
Amines
asymmetric catalysis
Bearing
Carbon
Catalysts
chirality
Ethers
Fluorination
fluorine
Formations
Michael reaction
Olefins
organocatalysis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Four C′s: The chiral secondary amine phosphoramide A was developed and serves as a powerful catalyst for the 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. TMS=trimethylsilyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201501747