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1 article(s) from Brunet, Vincent A

Three step synthesis of single diastereoisomers of the vicinal trifluoro motif

Vincent A. Brunet,
Alexandra M. Z. Slawin and
David O'Hagan

Beilstein J. Org. Chem. 2009, 5, No. 61, doi:10.3762/bjoc.5.61

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Graphical Abstract

Scheme 1: Previous six step route to the vicinal all-syn-trifluoro motif.

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Scheme 2: Novel three step successive fluorination strategy from α,β-epoxy alcohols to different diastereoiso...

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Scheme 3: Synthesis approach to the requisite α,β-epoxy alcohols 6b and 7b.

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Figure 1: X-ray structure (CCDC 750307) and stereochemistry of α,β-epoxy alcohol 7b.

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Figure 2: X-ray structure (CCDC 750306) and stereochemistry of α,β-epoxy alcohol 7a.

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Scheme 4: Three step sequential fluorination from α,β-epoxy alcohols to eg. the vicinyltrifluoro tosylate 11.

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Scheme 5: Unexpected cyclisation of 9b to furan 14 with HF·pyridine. An X-ray structure of 14 (CCDC 750309) r...

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Scheme 6: Epoxide ring opening of 9b with 3HF·Et₃N required forcing conditions. The structure and stereochemi...

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Scheme 7: Three step sequential fluorination from α,β-epoxy alcohol 7b to vicinal trifluoro tosylate 17b.

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Scheme 8: Epoxide ring opening with 3HF∙Et₃N and synthesis of the all-syn vicinal trifluoro tosylate 17a.

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Published 05 Nov 2009

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