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Beilstein J. Org. Chem. 2009, 5, No. 61, doi:10.3762/bjoc.5.61
Previous six step route to the vicinal all-syn-trifluoro motif.
Novel three step successive fluorination strategy from α,β-epoxy alcohols to different diastereoiso...
Synthesis approach to the requisite α,β-epoxy alcohols 6b and 7b.
X-ray structure (CCDC 750307) and stereochemistry of α,β-epoxy alcohol 7b.
X-ray structure (CCDC 750306) and stereochemistry of α,β-epoxy alcohol 7a.
Three step sequential fluorination from α,β-epoxy alcohols to eg. the vicinyltrifluoro tosylate 11.
Unexpected cyclisation of 9b to furan 14 with HF·pyridine. An X-ray structure of 14 (CCDC 750309) r...
Epoxide ring opening of 9b with 3HF·Et3N required forcing conditions. The structure and stereochemi...
Three step sequential fluorination from α,β-epoxy alcohol 7b to vicinal trifluoro tosylate 17b.
Epoxide ring opening with 3HF∙Et3N and synthesis of the all-syn vicinal trifluoro tosylate 17a.