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

Jin Sheng Yu
, Fu Min Liao
, Wei Ming Gao
, Kui Liao
, Run Lin Zuo
, Jian Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University
Luzhou High School
Nankai University

Research output: Contribution to journal › Article › peer-review

201 Scopus citations

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.

Original language	English
Pages (from-to)	7381-7385
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	25
DOIs	https://doi.org/10.1002/anie.201501747
State	Published - 1 Jun 2015

Keywords

amines
asymmetric catalysis
chirality
fluorine
organocatalysis

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10.1002/anie.201501747

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

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",

author = "Yu, \{Jin Sheng\} and Liao, \{Fu Min\} and Gao, \{Wei Ming\} and Kui Liao and Zuo, \{Run Lin\} and Jian Zhou",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2015",

month = jun,

day = "1",

doi = "10.1002/anie.201501747",

language = "英语",

volume = "54",

pages = "7381--7385",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

number = "25",

}

TY - JOUR

T1 - Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers

T2 - Formation of Quaternary Carbon Stereocenters

AU - Yu, Jin Sheng

AU - Liao, Fu Min

AU - Gao, Wei Ming

AU - Liao, Kui

AU - Zuo, Run Lin

AU - Zhou, Jian

PY - 2015/6/1

Y1 - 2015/6/1

N2 - 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.

AB - 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.

KW - amines

KW - asymmetric catalysis

KW - chirality

KW - fluorine

KW - organocatalysis

UR - https://www.scopus.com/pages/publications/85027955101

U2 - 10.1002/anie.201501747

DO - 10.1002/anie.201501747

M3 - 文章

AN - SCOPUS:85027955101

SN - 1433-7851

VL - 54

SP - 7381

EP - 7385

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 25

ER -

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

Abstract

Keywords

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