Highly functionalised difluorinated cyclohexenols

P J Crowley; A.C. Moralee; Jonathan Percy; N.S. Spencer

doi:10.1055/s-2000-8688

Highly functionalised difluorinated cyclohexenols

P J Crowley, A.C. Moralee, Jonathan Percy, N.S. Spencer

Pure And Applied Chemistry

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

8 Citations (Scopus)

Abstract

Alkenoate 5 prepared on a multigramme scale from trifluoroethanol underwent cycloaddition with furan in good yield. Reduction of the ester group in the endo-cycloadduct 7a with DIBAl-H also resulted in decarbamoylation to reveal a diol which was protected as an acetonide 10. Various methods for nucleophilic ring opening were explored releasing highly functionalised difluorinated cyclohexenols, and suggesting a novel route to difluorinated analogues of cyclitols and monosaccharides.

Original language	English
Pages (from-to)	1737-1740
Number of pages	4
Journal	Synlett
Volume	2000
Issue number	12
DOIs	https://doi.org/10.1055/s-2000-8688
Publication status	Published - 2000

Keywords

difluoroalkenoate
fluorinated dienophile
Stille
Diels-Alder
ring opening

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abstract = "Alkenoate 5 prepared on a multigramme scale from trifluoroethanol underwent cycloaddition with furan in good yield. Reduction of the ester group in the endo-cycloadduct 7a with DIBAl-H also resulted in decarbamoylation to reveal a diol which was protected as an acetonide 10. Various methods for nucleophilic ring opening were explored releasing highly functionalised difluorinated cyclohexenols, and suggesting a novel route to difluorinated analogues of cyclitols and monosaccharides. ",

keywords = "difluoroalkenoate, fluorinated dienophile, Stille, Diels-Alder , ring opening",

author = "Crowley, {P J} and A.C. Moralee and Jonathan Percy and N.S. Spencer",

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doi = "10.1055/s-2000-8688",

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T1 - Highly functionalised difluorinated cyclohexenols

AU - Crowley, P J

AU - Moralee, A.C.

AU - Percy, Jonathan

AU - Spencer, N.S.

PY - 2000

Y1 - 2000

N2 - Alkenoate 5 prepared on a multigramme scale from trifluoroethanol underwent cycloaddition with furan in good yield. Reduction of the ester group in the endo-cycloadduct 7a with DIBAl-H also resulted in decarbamoylation to reveal a diol which was protected as an acetonide 10. Various methods for nucleophilic ring opening were explored releasing highly functionalised difluorinated cyclohexenols, and suggesting a novel route to difluorinated analogues of cyclitols and monosaccharides.

AB - Alkenoate 5 prepared on a multigramme scale from trifluoroethanol underwent cycloaddition with furan in good yield. Reduction of the ester group in the endo-cycloadduct 7a with DIBAl-H also resulted in decarbamoylation to reveal a diol which was protected as an acetonide 10. Various methods for nucleophilic ring opening were explored releasing highly functionalised difluorinated cyclohexenols, and suggesting a novel route to difluorinated analogues of cyclitols and monosaccharides.

KW - difluoroalkenoate

KW - fluorinated dienophile

KW - Stille

KW - Diels-Alder

KW - ring opening

U2 - 10.1055/s-2000-8688

DO - 10.1055/s-2000-8688

M3 - Article

SN - 0936-5214

VL - 2000

SP - 1737

EP - 1740

JO - Synlett

JF - Synlett

IS - 12

ER -

Highly functionalised difluorinated cyclohexenols

Abstract

Keywords

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