Palladium-(S,pR)-FerroNPS-catalyzed asymmetric allylic etherification: Electronic effect of nonconjugated substituents on benzylic alcohols on enantioselectivity

Fuk Loi Lam; Terry Tin Lok Au-Yeung; Fuk Yee Kwong; Zhongyuan Zhou; Kwok Yin Wong; Albert S.C. Chan

doi:10.1002/anie.200703955

Palladium-(S,_pR)-FerroNPS-catalyzed asymmetric allylic etherification: Electronic effect of nonconjugated substituents on benzylic alcohols on enantioselectivity

Fuk Loi Lam, Terry Tin Lok Au-Yeung, Fuk Yee Kwong, Zhongyuan Zhou, Kwok Yin Wong, Albert S.C. Chan

Research output: Journal article publication › Journal article › Academic research › peer-review

92 Citations (Scopus)

Abstract

(Chemical Equation Presented) An enantioselective C-O bond-forming reaction proceeds well under palladium catalysis with newly developed N-P,S ligands with a ferrocene motif (see scheme). Nonconjugated substituents on the benzylic alcohol substrate lead to an increase in enantioselectivity with increasing electron-donating ability in the title reaction with racemic 1,3-diphenyl-2-propenyl acetate. Cy = cyclohexyl. KGaA.

Original language	English
Pages (from-to)	1280-1283
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	7
DOIs	https://doi.org/10.1002/anie.200703955
Publication status	Published - 1 Feb 2008

Keywords

Asymmetric catalysis
Electronic effects
Etherification
P,S ligands
Palladium

ASJC Scopus subject areas

Catalysis
General Chemistry

More information

10.1002/anie.200703955

Cite this

@article{bf8cb59d6fbb4489ab3ff4404285642f,

title = "Palladium-(S,pR)-FerroNPS-catalyzed asymmetric allylic etherification: Electronic effect of nonconjugated substituents on benzylic alcohols on enantioselectivity",

abstract = "(Chemical Equation Presented) An enantioselective C-O bond-forming reaction proceeds well under palladium catalysis with newly developed N-P,S ligands with a ferrocene motif (see scheme). Nonconjugated substituents on the benzylic alcohol substrate lead to an increase in enantioselectivity with increasing electron-donating ability in the title reaction with racemic 1,3-diphenyl-2-propenyl acetate. Cy = cyclohexyl. KGaA.",

keywords = "Asymmetric catalysis, Electronic effects, Etherification, P,S ligands, Palladium",

author = "Lam, {Fuk Loi} and Au-Yeung, {Terry Tin Lok} and Kwong, {Fuk Yee} and Zhongyuan Zhou and Wong, {Kwok Yin} and Chan, {Albert S.C.}",

year = "2008",

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publisher = "John Wiley and Sons Ltd",

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Palladium-(S,_pR)-FerroNPS-catalyzed asymmetric allylic etherification: Electronic effect of nonconjugated substituents on benzylic alcohols on enantioselectivity. / Lam, Fuk Loi; Au-Yeung, Terry Tin Lok; Kwong, Fuk Yee et al.
In: Angewandte Chemie - International Edition, Vol. 47, No. 7, 01.02.2008, p. 1280-1283.

Research output: Journal article publication › Journal article › Academic research › peer-review

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T1 - Palladium-(S,pR)-FerroNPS-catalyzed asymmetric allylic etherification: Electronic effect of nonconjugated substituents on benzylic alcohols on enantioselectivity

AU - Lam, Fuk Loi

AU - Au-Yeung, Terry Tin Lok

AU - Kwong, Fuk Yee

AU - Zhou, Zhongyuan

AU - Wong, Kwok Yin

AU - Chan, Albert S.C.

PY - 2008/2/1

Y1 - 2008/2/1

N2 - (Chemical Equation Presented) An enantioselective C-O bond-forming reaction proceeds well under palladium catalysis with newly developed N-P,S ligands with a ferrocene motif (see scheme). Nonconjugated substituents on the benzylic alcohol substrate lead to an increase in enantioselectivity with increasing electron-donating ability in the title reaction with racemic 1,3-diphenyl-2-propenyl acetate. Cy = cyclohexyl. KGaA.

AB - (Chemical Equation Presented) An enantioselective C-O bond-forming reaction proceeds well under palladium catalysis with newly developed N-P,S ligands with a ferrocene motif (see scheme). Nonconjugated substituents on the benzylic alcohol substrate lead to an increase in enantioselectivity with increasing electron-donating ability in the title reaction with racemic 1,3-diphenyl-2-propenyl acetate. Cy = cyclohexyl. KGaA.

KW - Asymmetric catalysis

KW - Electronic effects

KW - Etherification

KW - P,S ligands

KW - Palladium

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DO - 10.1002/anie.200703955

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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