Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate.

James A B Laurenson, John A Parkinson, Jonathan M Percy, Giuseppe Rinaudo, Ricard Roig

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Article in Beilstein journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors.

James A B LaurensonWestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom ; Carbosynth Ltd., 93 Innovation Drive, Milton Park, Abingdon, Oxfordshire OX14 4RZ, United Kingdom.

John A ParkinsonWestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.

Jonathan M PercyWestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.

Giuseppe RinaudoWestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.

Ricard RoigDepartment of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, United Kingdom ; Lallemand Gb Ingredients, Dock Road, Felixstowe, Suffolk IP11 3QW, United Kingdom.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Esters of crotonic acid were brominated on a multigramme scale using a free radical procedure. A phase transfer catalysed fluorination transformed these species to the 4-fluorobut-2E-enoates reproducibly and at scale (48-53%, ca. 300 mmol). Asymmetric dihydroxylation reactions were then used to transform the butenoate, ultimately into all four diastereoisomers of a versatile fluorinated C4 building block at high enantiomeric-enrichment. The (DHQ)2AQN and (DHQD)2AQN ligands described by Sharpless were the most effective. The development and optimisation of a new and facile method for the determination of ee is also described; (19)F{(1)H} spectra recorded in d-chloroform/diisopropyl tartrate showed distinct baseline separated signals for different enantiomers.

Indexed as

asymmetricdihydroxylationee determinationfluorinationfluorosugarsorgano-fluorine

Identifiers

PMID24367430

DOI10.3762/bjoc.9.301

PMCPMC3869297

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