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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.

SUBMITTER: Yang Q

PROVIDER: S-EPMC3878608 | biostudies-other | 2013 Dec

REPOSITORIES: biostudies-other

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

Yang Qingliang Q Njardarson Jon T JT

Tetrahedron letters 20131201 51

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 a ...[more]

PMID: 24391289

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