Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle

Vasudevan Dhayalan; Kanchan Mal; Anat Milo

doi:10.1055/s-0037-1611786

Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle

Vasudevan Dhayalan, Kanchan Mal, Anat Milo

Department of Chemistry

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

7 Scopus citations

Abstract

A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.

Original language	English
Pages (from-to)	2845-2864
Number of pages	20
Journal	Synthesis (Germany)
Volume	51
Issue number	14
DOIs	https://doi.org/10.1055/s-0037-1611786
State	Published - 1 Jan 2019

Keywords

N-heterocyclic carbenes
arylhydrazines
benzyl alcohol
desilylation
organocatalysis
organomagnesium reagents
protecting groups
triazolium salts

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0037-1611786

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title = "Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle",

abstract = "A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.",

keywords = "N-heterocyclic carbenes, arylhydrazines, benzyl alcohol, desilylation, organocatalysis, organomagnesium reagents, protecting groups, triazolium salts",

author = "Vasudevan Dhayalan and Kanchan Mal and Anat Milo",

note = "Funding Information: This work was supported by the Israel Science Foundation (Grant No. 14-50-00126). V.D. gratefully acknowledges the Israeli Council for Higher Education's Planning and Budgeting Committee (PBC) for a postdoctoral fellowship. K.M. gratefully acknowledges the Kreitman Graduate School for a postdoctoral fellowship.IsraelScienceFoundation(1193/17) Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart New York.",

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doi = "10.1055/s-0037-1611786",

language = "English",

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AU - Dhayalan, Vasudevan

AU - Mal, Kanchan

AU - Milo, Anat

N1 - Funding Information: This work was supported by the Israel Science Foundation (Grant No. 14-50-00126). V.D. gratefully acknowledges the Israeli Council for Higher Education's Planning and Budgeting Committee (PBC) for a postdoctoral fellowship. K.M. gratefully acknowledges the Kreitman Graduate School for a postdoctoral fellowship.IsraelScienceFoundation(1193/17) Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2019/1/1

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N2 - A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.

AB - A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.

KW - N-heterocyclic carbenes

KW - arylhydrazines

KW - benzyl alcohol

KW - desilylation

KW - organocatalysis

KW - organomagnesium reagents

KW - protecting groups

KW - triazolium salts

UR - http://www.scopus.com/inward/record.url?scp=85068184396&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1611786

DO - 10.1055/s-0037-1611786

M3 - Article

AN - SCOPUS:85068184396

SN - 0039-7881

VL - 51

SP - 2845

EP - 2864

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 14

ER -

Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle

Abstract

Keywords

ASJC Scopus subject areas

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