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Regioselective Mukaiyama hydroperoxysilylation of 2-alkyl- or 2-aryl-prop-2-en-1-ols: application to a new synthesis of 1,2,4-trioxanes

✍ Scribed by Paul M O'Neill; Matthew Pugh; Jill Davies; Stephen A Ward; B.Kevin Park

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 85 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00791-2

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✦ Synopsis

Co(II)-mediated peroxysilylation of allylic alcohols 6 or 9 regioselectively provides peroxysilyl alcohols 7 and 10 in good yield. Reaction of these peroxysilyl alcohols with aldehydes or ketones provides target 1,2,4-trioxanes in good to excellent yields. The sequence of Markovnikov hydroperoxysilylation and subsequent reaction with a carbonyl compound can also be readily achieved in a one-pot procedure. Significantly, easily prepared trioxanes 11a and 11b have potent in vitro antimalarial activity versus chloroquine resistant K1 Plasmodium falciparum.

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