Chemo- and diastereoselective Bi(OTf)3-catalyzed benzylation of silyl nucleophiles

Philipp Rubenbauer; Thorsten Bach

doi:10.1016/j.tetlet.2007.12.092

Chemo- and diastereoselective Bi(OTf)₃-catalyzed benzylation of silyl nucleophiles

Philipp Rubenbauer, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich

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

38 Scopus citations

Abstract

The direct alkylation of silyl enol ethers with para-methoxybenzylic alcohols or their corresponding acetates was efficiently catalyzed by Bi(OTf)₃ in CH₃NO₂ as the solvent. The reaction provided the α-benzylated carbonyl compounds in high yields after short reaction times using 1-2.5 mol % of the catalyst. Benzylic acetates other than para-methoxybenzylic acetates also underwent the reaction. High facial diastereoselectivities were observed with acetates derived from chiral α-branched para-methoxybenzylic alcohols. In addition, a catalytic reduction with Et₃SiH as the reducing agent is reported.

Original language	English
Pages (from-to)	1305-1309
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2007.12.092
State	Published - 18 Feb 2008

Keywords

Benzylic alcohols
Bi catalysis
Facial diastereoselectivity
Silyl enol ether
Triethylsilane

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10.1016/j.tetlet.2007.12.092

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title = "Chemo- and diastereoselective Bi(OTf)3-catalyzed benzylation of silyl nucleophiles",

abstract = "The direct alkylation of silyl enol ethers with para-methoxybenzylic alcohols or their corresponding acetates was efficiently catalyzed by Bi(OTf)3 in CH3NO2 as the solvent. The reaction provided the α-benzylated carbonyl compounds in high yields after short reaction times using 1-2.5 mol % of the catalyst. Benzylic acetates other than para-methoxybenzylic acetates also underwent the reaction. High facial diastereoselectivities were observed with acetates derived from chiral α-branched para-methoxybenzylic alcohols. In addition, a catalytic reduction with Et3SiH as the reducing agent is reported.",

keywords = "Benzylic alcohols, Bi catalysis, Facial diastereoselectivity, Silyl enol ether, Triethylsilane",

author = "Philipp Rubenbauer and Thorsten Bach",

note = "Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft, by the graduate college NanoCat (scholarship to P.R.) and by the Fonds der Chemischen Industrie.",

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doi = "10.1016/j.tetlet.2007.12.092",

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T1 - Chemo- and diastereoselective Bi(OTf)3-catalyzed benzylation of silyl nucleophiles

AU - Rubenbauer, Philipp

AU - Bach, Thorsten

N1 - Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft, by the graduate college NanoCat (scholarship to P.R.) and by the Fonds der Chemischen Industrie.

PY - 2008/2/18

Y1 - 2008/2/18

N2 - The direct alkylation of silyl enol ethers with para-methoxybenzylic alcohols or their corresponding acetates was efficiently catalyzed by Bi(OTf)3 in CH3NO2 as the solvent. The reaction provided the α-benzylated carbonyl compounds in high yields after short reaction times using 1-2.5 mol % of the catalyst. Benzylic acetates other than para-methoxybenzylic acetates also underwent the reaction. High facial diastereoselectivities were observed with acetates derived from chiral α-branched para-methoxybenzylic alcohols. In addition, a catalytic reduction with Et3SiH as the reducing agent is reported.

AB - The direct alkylation of silyl enol ethers with para-methoxybenzylic alcohols or their corresponding acetates was efficiently catalyzed by Bi(OTf)3 in CH3NO2 as the solvent. The reaction provided the α-benzylated carbonyl compounds in high yields after short reaction times using 1-2.5 mol % of the catalyst. Benzylic acetates other than para-methoxybenzylic acetates also underwent the reaction. High facial diastereoselectivities were observed with acetates derived from chiral α-branched para-methoxybenzylic alcohols. In addition, a catalytic reduction with Et3SiH as the reducing agent is reported.

KW - Benzylic alcohols

KW - Bi catalysis

KW - Facial diastereoselectivity

KW - Silyl enol ether

KW - Triethylsilane

UR - http://www.scopus.com/inward/record.url?scp=38349167247&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2007.12.092

DO - 10.1016/j.tetlet.2007.12.092

M3 - Article

AN - SCOPUS:38349167247

SN - 0040-4039

VL - 49

SP - 1305

EP - 1309

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Chemo- and diastereoselective Bi(OTf)₃-catalyzed benzylation of silyl nucleophiles

Abstract

Keywords

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