Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group

Qingliang Yang; Jon T. Njardarson

doi:10.1016/j.tetlet.2013.10.097

Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group

Qingliang Yang, Jon T. Njardarson

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

18 Scopus citations

Abstract

A trifluoroethyl (TFE) ether is specifically introduced as a protecting group in organic chemistry. Its first strategic application and removal in the total synthesis of vinigrol is discussed. Two lithium base mediated deprotection strategies for its removal are presented in this Letter. In one deprotection approach, the trifluoroethyl ether is converted to a difluorovinyl ether and then catalytically cleaved using osmium tetraoxide, while in the second approach a difluorovinyl anion is formed and trapped with an electrophilic oxygen reagent (MoOPH) to form a labile difluoroacetate. To further aid the reader, a summary of approaches for forming trifluoroethyl ethers is included as well as a discussion of alternate deprotection strategies.

Original language	English (US)
Pages (from-to)	7080-7082
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2013.10.097
State	Published - Dec 18 2013
Externally published	Yes

Keywords

Deprotection
Difluorovinyl
Dihydroxylation
Electrophilic oxygen
Trifluoroethyl ether

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.10.097

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title = "Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group",

abstract = "A trifluoroethyl (TFE) ether is specifically introduced as a protecting group in organic chemistry. Its first strategic application and removal in the total synthesis of vinigrol is discussed. Two lithium base mediated deprotection strategies for its removal are presented in this Letter. In one deprotection approach, the trifluoroethyl ether is converted to a difluorovinyl ether and then catalytically cleaved using osmium tetraoxide, while in the second approach a difluorovinyl anion is formed and trapped with an electrophilic oxygen reagent (MoOPH) to form a labile difluoroacetate. To further aid the reader, a summary of approaches for forming trifluoroethyl ethers is included as well as a discussion of alternate deprotection strategies.",

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T1 - Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group

AU - Yang, Qingliang

AU - Njardarson, Jon T.

PY - 2013/12/18

Y1 - 2013/12/18

N2 - A trifluoroethyl (TFE) ether is specifically introduced as a protecting group in organic chemistry. Its first strategic application and removal in the total synthesis of vinigrol is discussed. Two lithium base mediated deprotection strategies for its removal are presented in this Letter. In one deprotection approach, the trifluoroethyl ether is converted to a difluorovinyl ether and then catalytically cleaved using osmium tetraoxide, while in the second approach a difluorovinyl anion is formed and trapped with an electrophilic oxygen reagent (MoOPH) to form a labile difluoroacetate. To further aid the reader, a summary of approaches for forming trifluoroethyl ethers is included as well as a discussion of alternate deprotection strategies.

AB - A trifluoroethyl (TFE) ether is specifically introduced as a protecting group in organic chemistry. Its first strategic application and removal in the total synthesis of vinigrol is discussed. Two lithium base mediated deprotection strategies for its removal are presented in this Letter. In one deprotection approach, the trifluoroethyl ether is converted to a difluorovinyl ether and then catalytically cleaved using osmium tetraoxide, while in the second approach a difluorovinyl anion is formed and trapped with an electrophilic oxygen reagent (MoOPH) to form a labile difluoroacetate. To further aid the reader, a summary of approaches for forming trifluoroethyl ethers is included as well as a discussion of alternate deprotection strategies.

KW - Deprotection

KW - Difluorovinyl

KW - Dihydroxylation

KW - Electrophilic oxygen

KW - Trifluoroethyl ether

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DO - 10.1016/j.tetlet.2013.10.097

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group

Abstract

Keywords

ASJC Scopus subject areas

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