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. 2010 Jul 21;132(28):9558-60.
doi: 10.1021/ja103331t.

Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt

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Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt

Ravi P Singh et al. J Am Chem Soc. .

Abstract

Despite their synthetic significance there is a general lack of asymmetric vinylogous aldol reactions that tolerate variations of both the silyloxy furans and aldehydes. We have developed a new chiral organic catalyst based on a carboxylate-ammonium salt prepared from a thiourea-amine and a carboxylic acid. This new catalyst enabled us to develop an efficient asymmetric vinylogous aldol reaction of unprecedented scope with respect to both 2-trimethylsilyloxy furans and aldehydes.

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Figures

Figure 1
Figure 1
The structure of Cinchona Alkaloid Catalysts
Scheme 1
Scheme 1
Plausible Catalytic Cycle for Vinylogous Aldol Reaction

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