A sequential transformation based on a titanium-mediated aldol reaction from chiral α-tert-butyldimethylsilyloxy ketones followed by reduction of the resultant aldolates with LiBH 4 provides a straightforward access to syn-1,3-diols. These diols, containing up to three new stereocentres, can
A sequential transformation based on the titanium-mediated aldol addition of (S)-1-bromo-3-(tert-butyldimethylsilyloxy)-2-butanone, a chiral lactate-derived ketone, to tetradecanal followed by reduction of the ensuing aldolate afforded the corresponding syn-1,3-diol as a single diastereomer. Debro-
Highly Stereoselective Synthesis of syn-1,3-Diols Through a Sequential Titanium--Mediated Aldol Reaction and LiBH4 Reduction. -(ESTEVE, J.; MATAS, S.; PELLICENA, M.; VELASCO, J.; ROMEA, P.; URPI*, F.; FONT-BARDIA, M.; Eur.
Highly Stereoselective Titanium-Mediated Aldol Reactions from Chiral α-Silyloxy Ketones. A Reliable Tool for the Synthesis of Natural Products. -The influence of substitution pattern of α-siloxy ketones on the reactivity in Ti-mediated aldol reactions is studied. The reaction affords syn,syn-products with excellent diastereoselectivity, irrespective of the substituents applied. Further manipulation of the initial aldol adducts is studied, including removal of the original stereocenter [cf. (V)] and stereoselective reduction of the carbonyl group [cf. (XI)]. A variety of polyol derivatives can be achieved, which represent key subunits of natural or bioactive products [cf. NFX-2 (IX), antimycinone or salinomycin]. -(ESTEVE, J.; JIMENEZ, C.; NEBOT, J.; VELASCO, J.; ROMEA*, P.; URPI, F.; Tetrahedron 67 (2011) 33, 6045-6056, http://dx.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.