A stereodivergent asymmetric approach to difluorinated aldonic acids

Christophe Audouard, Igor Barsukov, John Fawcett, Gerry A. Griffith, Jonathan M. Percy, Stéphane Pintat, Clive A. Smith
2004 Chemical Communications  
Clive A (2004) A stereodivergent asymmetric approach to difluorinated aldonic acids. Chemical Communications (13). A (bromodifluoromethyl)alkyne has been deployed in a stereoselective route to difluorinated aldonic acid analogues, in which a Sharpless asymmetric dihydroxylation reaction and diastereoisomer separation set the stage for phenyl group oxidation. † † Electronic supplementary information (ESI) available: preparation of 1 and 2a, NMR and electrospray for 14 (deuterium exchanged),
more » ... um exchanged), chiral HPLC traces for 7a and 7b, optical rotations for 7a-8b. See http://www.rsc.org/ suppdata/cc/b4/b405067c/ Scheme 1 Retrosynthetic analysis and identification of pivotal intermediate Scheme 2 Developing an addition methodology (see text). 5 2 6 C h e m . C o m m u n . , 2 0 0 4 , 1 5 2 6 -1 5 2 7
doi:10.1039/b405067c pmid:15216363 fatcat:pwbmnods3jcwjbybvn6f2wllzy