Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides

Raffaele Senatore; Laura Ielo; Ernst Urban; Wolfgang Holzer; Vittorio Pace

doi:10.1002/ejoc.201800095

Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides

Raffaele Senatore
, Laura Ielo
, Ernst Urban
, Wolfgang Holzer
, Vittorio Pace (Corresponding author)

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

The proper generation of α-thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-oxo thioethers. The procedure is adaptable to alkyl- or aryl- thiomethyllithium conjugates. It has the advantages of conceptual simplicity and versatility of the addn. of organometallics to Weinreb amides with the possibility to fully preserve the optical information contained in the starting materials.

Original language	English
Pages (from-to)	2466-2470
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	20-21
DOIs	https://doi.org/10.1002/ejoc.201800095
Publication status	Published - 7 Jun 2018

Funding

The authors thank the University of Vienna for generous support, MSc L. Urtis and MSc F. Patane for experimental assistance, and MSc. D. Dobusch for HRMS analysis. R. S. acknowledges the OEAD for a predoctoral Ernst Mach grant.

Austrian Fields of Science 2012

104015 Organic chemistry

Keywords

Homologation
Lithiation
Weinreb amides
Sulfur
Ketones
SULFENYLATED CARBONYL-COMPOUNDS
CHLOROMETHYL ETHYL ETHER
EFFICIENT SYNTHESIS
LITHIUM CARBENOIDS
KETO THIOETHERS
STRAIGHTFORWARD ACCESS
ORGANIC-SYNTHESIS
HIGHLY EFFICIENT
BOND FORMATION
ISOCYANATES
REAGENTS
HALOMETHYLLITHIUMS
CATALYST

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10.1002/ejoc.201800095

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title = "Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides",

abstract = "The proper generation of α-thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-oxo thioethers. The procedure is adaptable to alkyl- or aryl- thiomethyllithium conjugates. It has the advantages of conceptual simplicity and versatility of the addn. of organometallics to Weinreb amides with the possibility to fully preserve the optical information contained in the starting materials.",

keywords = "Homologation, Lithiation, Weinreb amides, Sulfur, Ketones, SULFENYLATED CARBONYL-COMPOUNDS, CHLOROMETHYL ETHYL ETHER, EFFICIENT SYNTHESIS, LITHIUM CARBENOIDS, KETO THIOETHERS, STRAIGHTFORWARD ACCESS, ORGANIC-SYNTHESIS, HIGHLY EFFICIENT, BOND FORMATION, ISOCYANATES, REAGENTS, HALOMETHYLLITHIUMS, CATALYST",

author = "Raffaele Senatore and Laura Ielo and Ernst Urban and Wolfgang Holzer and Vittorio Pace",

note = "Funding Information: The authors thank the University of Vienna for generous support, MSc L. Urtis and MSc F. Patan{\`e} for experimental assistance, and MSc. D. Dobusch for HRMS analysis. R. S. acknowledges the OEAD for a predoctoral Ernst Mach grant. Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = jun,

day = "7",

doi = "10.1002/ejoc.201800095",

language = "English",

volume = "2018",

pages = "2466--2470",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "20-21",

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TY - JOUR

T1 - Substituted α-Sulfur Methyl Carbanions

T2 - Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides

AU - Senatore, Raffaele

AU - Ielo, Laura

AU - Urban, Ernst

AU - Holzer, Wolfgang

AU - Pace, Vittorio

N1 - Funding Information: The authors thank the University of Vienna for generous support, MSc L. Urtis and MSc F. Patanè for experimental assistance, and MSc. D. Dobusch for HRMS analysis. R. S. acknowledges the OEAD for a predoctoral Ernst Mach grant. Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/6/7

Y1 - 2018/6/7

N2 - The proper generation of α-thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-oxo thioethers. The procedure is adaptable to alkyl- or aryl- thiomethyllithium conjugates. It has the advantages of conceptual simplicity and versatility of the addn. of organometallics to Weinreb amides with the possibility to fully preserve the optical information contained in the starting materials.

AB - The proper generation of α-thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-oxo thioethers. The procedure is adaptable to alkyl- or aryl- thiomethyllithium conjugates. It has the advantages of conceptual simplicity and versatility of the addn. of organometallics to Weinreb amides with the possibility to fully preserve the optical information contained in the starting materials.

KW - Homologation

KW - Lithiation

KW - Weinreb amides

KW - Sulfur

KW - Ketones

KW - SULFENYLATED CARBONYL-COMPOUNDS

KW - CHLOROMETHYL ETHYL ETHER

KW - EFFICIENT SYNTHESIS

KW - LITHIUM CARBENOIDS

KW - KETO THIOETHERS

KW - STRAIGHTFORWARD ACCESS

KW - ORGANIC-SYNTHESIS

KW - HIGHLY EFFICIENT

KW - BOND FORMATION

KW - ISOCYANATES

KW - REAGENTS

KW - HALOMETHYLLITHIUMS

KW - CATALYST

UR - https://www.scopus.com/pages/publications/85046029135

U2 - 10.1002/ejoc.201800095

DO - 10.1002/ejoc.201800095

M3 - Article

SN - 1434-193X

VL - 2018

SP - 2466

EP - 2470

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 20-21

ER -

Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides

Abstract

Funding

Austrian Fields of Science 2012

Keywords

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