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1 article(s) from Parkinson, John A

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

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

Beilstein J. Org. Chem. 2013, 9, 2660–2668, doi:10.3762/bjoc.9.301

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Scheme 1: Key steps from the synthesis of 6-fluoro-D-olivose (6) from D-glucose (1).

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Scheme 2: De novo asymmetric syntheses of 6-deoxy-6-fluorohexoses [13].

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Scheme 3: Fluorobutenoate building block 14, and related species 16 and 19 from the literature [14-16].

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Scheme 4: Fluorobutenoate building blocks 25 and 26 prepared from crotonic acid.

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Figure 1: Side product 27 isolated from attempted fluorination.

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Figure 2: The ligand panel used in the asymmetric dihydroxylation studies. The bold oxygen shows the point of...

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Scheme 5: Typical AD procedure; see Table 1 for outcomes.

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Scheme 6: Conversion of enantiomerically-enriched diols to dibenzoates for HPLC analysis.

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Figure 3: Diisopropyl L-tartrate (30) used as a chiral modifier for NMR determination of ee.

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Figure 4: Partial ¹⁹F{¹H} NMR spectra (376 MHz, L-(+)-DIPT/CDCl₃, 300 K) spectra of (a) racemate 28c, (b) dio...

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Figure 5: Partial ¹⁹F{¹H} NMR (400 MHz, L-(+)-DIPT/CDCl₃, 300 K) spectra of 28b and 28a using optimised condi...

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Scheme 7: Applying cyclic sulfate methodology to gain access to anti-diastereoisomers (transformations were d...

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Scheme 8: Protecting and chain extending the educts of asymmetric dihydroxylation.

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Published 26 Nov 2013

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