Purification-Free Preparation of Trifluoroacetimidoyl Chlorides and Their Use in Catalytic Chemical Glycosylation

Nikolai Cordua; Signe R. Steffensen; Andrea G. Mascherpa; Louise G. Christensen; Henrik H. Jensen

doi:10.1021/acs.orglett.4c04525

Purification-Free Preparation of Trifluoroacetimidoyl Chlorides and Their Use in Catalytic Chemical Glycosylation

Nikolai Cordua, Signe R. Steffensen, Andrea G. Mascherpa, Louise G. Christensen, Henrik H. Jensen^*

^*Corresponding author af dette arbejde

Institut for Kemi

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

Abstract

This Letter describes a purification-free method for synthesizing 2,2,2-trifluoro-N-phenylacetimidoyl chloride and several related congeners from their corresponding amides using POCl₃ and pyridine. N-(2,4-Dichlorophenyl)-2,2,2-trifluoroacetimidoyl chloride demonstrated superior stability compared to 2,2,2-trifluoro-N-phenylacetimidoyl chloride, which is commonly used for glycosyl donor synthesis of the Yu-type. The described method also enabled a general and highly β-selective synthesis of trifluoroacetimidate glycosyl donors using DABCO in toluene. The donors were shown to undergo efficient glycosylation with various glycosyl acceptors.

Originalsprog	Engelsk
Tidsskrift	Organic Letters
Vol/bind	27
Nummer	7
Sider (fra-til)	1602-1607
Antal sider	6
ISSN	1523-7060
DOI	https://doi.org/10.1021/acs.orglett.4c04525
Status	Udgivet - feb. 2025

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title = "Purification-Free Preparation of Trifluoroacetimidoyl Chlorides and Their Use in Catalytic Chemical Glycosylation",

abstract = "This Letter describes a purification-free method for synthesizing 2,2,2-trifluoro-N-phenylacetimidoyl chloride and several related congeners from their corresponding amides using POCl3 and pyridine. N-(2,4-Dichlorophenyl)-2,2,2-trifluoroacetimidoyl chloride demonstrated superior stability compared to 2,2,2-trifluoro-N-phenylacetimidoyl chloride, which is commonly used for glycosyl donor synthesis of the Yu-type. The described method also enabled a general and highly β-selective synthesis of trifluoroacetimidate glycosyl donors using DABCO in toluene. The donors were shown to undergo efficient glycosylation with various glycosyl acceptors.",

author = "Nikolai Cordua and Steffensen, {Signe R.} and Mascherpa, {Andrea G.} and Christensen, {Louise G.} and Jensen, {Henrik H.}",

year = "2025",

month = feb,

doi = "10.1021/acs.orglett.4c04525",

language = "English",

volume = "27",

pages = "1602--1607",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "7",

}

Purification-Free Preparation of Trifluoroacetimidoyl Chlorides and Their Use in Catalytic Chemical Glycosylation. / Cordua, Nikolai; Steffensen, Signe R.; Mascherpa, Andrea G. et al.
I: Organic Letters, Bind 27, Nr. 7, 02.2025, s. 1602-1607.

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

TY - JOUR

T1 - Purification-Free Preparation of Trifluoroacetimidoyl Chlorides and Their Use in Catalytic Chemical Glycosylation

AU - Cordua, Nikolai

AU - Steffensen, Signe R.

AU - Mascherpa, Andrea G.

AU - Christensen, Louise G.

AU - Jensen, Henrik H.

PY - 2025/2

Y1 - 2025/2

N2 - This Letter describes a purification-free method for synthesizing 2,2,2-trifluoro-N-phenylacetimidoyl chloride and several related congeners from their corresponding amides using POCl3 and pyridine. N-(2,4-Dichlorophenyl)-2,2,2-trifluoroacetimidoyl chloride demonstrated superior stability compared to 2,2,2-trifluoro-N-phenylacetimidoyl chloride, which is commonly used for glycosyl donor synthesis of the Yu-type. The described method also enabled a general and highly β-selective synthesis of trifluoroacetimidate glycosyl donors using DABCO in toluene. The donors were shown to undergo efficient glycosylation with various glycosyl acceptors.

AB - This Letter describes a purification-free method for synthesizing 2,2,2-trifluoro-N-phenylacetimidoyl chloride and several related congeners from their corresponding amides using POCl3 and pyridine. N-(2,4-Dichlorophenyl)-2,2,2-trifluoroacetimidoyl chloride demonstrated superior stability compared to 2,2,2-trifluoro-N-phenylacetimidoyl chloride, which is commonly used for glycosyl donor synthesis of the Yu-type. The described method also enabled a general and highly β-selective synthesis of trifluoroacetimidate glycosyl donors using DABCO in toluene. The donors were shown to undergo efficient glycosylation with various glycosyl acceptors.

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U2 - 10.1021/acs.orglett.4c04525

DO - 10.1021/acs.orglett.4c04525

M3 - Journal article

AN - SCOPUS:85217547968

SN - 1523-7060

VL - 27

SP - 1602

EP - 1607

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Purification-Free Preparation of Trifluoroacetimidoyl Chlorides and Their Use in Catalytic Chemical Glycosylation

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