Highly enantioselective intermolecular alkylation of aldehydes with alcohols by cooperative catalysis of diarylprolinol silyl ether with Brønsted acid

Jian Xiao; Kai Zhao; Teck Peng Loh

doi:10.1002/asia.201100692

Highly enantioselective intermolecular alkylation of aldehydes with alcohols by cooperative catalysis of diarylprolinol silyl ether with Brønsted acid

Jian Xiao, Kai Zhao, Teck Peng Loh^*

^*Corresponding author for this work

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

70 Citations (Scopus)

Abstract

Two cooperative systems: I/2,3,4-trihydroxybenzoic acid and I/TfOH effect highly enantioselective intermolecular α-alkylation of aldehydes. These systems afford functionalized aldehydes in high yields, and with excellent ee and de values with broad substrate scope (see scheme; R¹=alkyl, R²,R³=aryl, or R²=ferrocenyl, R ³=phenyl, or R²=indolyl, R³=phenyl).

Original language	English
Pages (from-to)	2890-2894
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	6
Issue number	11
DOIs	https://doi.org/10.1002/asia.201100692
Publication status	Published - Nov 4 2011
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
General Chemistry
Organic Chemistry

Keywords

alkylation
brønsted acid
cooperative catalysis
enantioselectivty
organocatalysis

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10.1002/asia.201100692

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abstract = "Two cooperative systems: I/2,3,4-trihydroxybenzoic acid and I/TfOH effect highly enantioselective intermolecular α-alkylation of aldehydes. These systems afford functionalized aldehydes in high yields, and with excellent ee and de values with broad substrate scope (see scheme; R1=alkyl, R2,R3=aryl, or R2=ferrocenyl, R 3=phenyl, or R2=indolyl, R3=phenyl).",

keywords = "alkylation, br{\o}nsted acid, cooperative catalysis, enantioselectivty, organocatalysis",

author = "Jian Xiao and Kai Zhao and Loh, {Teck Peng}",

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doi = "10.1002/asia.201100692",

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T1 - Highly enantioselective intermolecular alkylation of aldehydes with alcohols by cooperative catalysis of diarylprolinol silyl ether with Brønsted acid

AU - Xiao, Jian

AU - Zhao, Kai

AU - Loh, Teck Peng

PY - 2011/11/4

Y1 - 2011/11/4

N2 - Two cooperative systems: I/2,3,4-trihydroxybenzoic acid and I/TfOH effect highly enantioselective intermolecular α-alkylation of aldehydes. These systems afford functionalized aldehydes in high yields, and with excellent ee and de values with broad substrate scope (see scheme; R1=alkyl, R2,R3=aryl, or R2=ferrocenyl, R 3=phenyl, or R2=indolyl, R3=phenyl).

AB - Two cooperative systems: I/2,3,4-trihydroxybenzoic acid and I/TfOH effect highly enantioselective intermolecular α-alkylation of aldehydes. These systems afford functionalized aldehydes in high yields, and with excellent ee and de values with broad substrate scope (see scheme; R1=alkyl, R2,R3=aryl, or R2=ferrocenyl, R 3=phenyl, or R2=indolyl, R3=phenyl).

KW - alkylation

KW - brønsted acid

KW - cooperative catalysis

KW - enantioselectivty

KW - organocatalysis

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JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 11

ER -

Highly enantioselective intermolecular alkylation of aldehydes with alcohols by cooperative catalysis of diarylprolinol silyl ether with Brønsted acid

Abstract

ASJC Scopus Subject Areas

Keywords

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