Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles

Zhiyong Jiang; Yuanhang Pan; Yujun Zhao; Ting Ma; Richmond Lee; Yuanyong Yang; Kuo Wei Huang; Ming Wah Wong; Choon Hong Tan

doi:10.1002/anie.200900964

Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles

Zhiyong Jiang, Yuanhang Pan, Yujun Zhao, Ting Ma, Richmond Lee, Yuanyong Yang, Kuo Wei Huang, Ming Wah Wong, Choon Hong Tan

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

141 Scopus citations

Abstract

The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results.

Original language	English (US)
Pages (from-to)	3627-3631
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	20
DOIs	https://doi.org/10.1002/anie.200900964
State	Published - May 4 2009
Externally published	Yes

Keywords

Asymmetric catalysis
Fluorine
Guanidine
Michael addition
Transition states

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200900964

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title = "Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles",

abstract = "The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results.",

keywords = "Asymmetric catalysis, Fluorine, Guanidine, Michael addition, Transition states",

author = "Zhiyong Jiang and Yuanhang Pan and Yujun Zhao and Ting Ma and Richmond Lee and Yuanyong Yang and Huang, {Kuo Wei} and Wong, {Ming Wah} and Tan, {Choon Hong}",

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doi = "10.1002/anie.200900964",

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Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles. / Jiang, Zhiyong; Pan, Yuanhang; Zhao, Yujun et al.
In: Angewandte Chemie - International Edition, Vol. 48, No. 20, 04.05.2009, p. 3627-3631.

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

TY - JOUR

T1 - Synthesis of a chiral quaternary carbon center bearing a fluorine atom

T2 - Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles

AU - Jiang, Zhiyong

AU - Pan, Yuanhang

AU - Zhao, Yujun

AU - Ma, Ting

AU - Lee, Richmond

AU - Yang, Yuanyong

AU - Huang, Kuo Wei

AU - Wong, Ming Wah

AU - Tan, Choon Hong

PY - 2009/5/4

Y1 - 2009/5/4

N2 - The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results.

AB - The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results.

KW - Asymmetric catalysis

KW - Fluorine

KW - Guanidine

KW - Michael addition

KW - Transition states

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JO - Angewandte Chemie - International Edition

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ER -

Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles

Abstract

Keywords

ASJC Scopus subject areas

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