Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes

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2010

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Abstract

The direct addition of enolizable aldehydes and a-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.

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Other article

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trifluoroethyl thioesters, polyketide synthases, ketones, triethylamine, bases, chemistry, multidisciplinary

Citation

Sauer,Scott J.;Garnsey,Michelle R.;Coltart,Don M.. 2010. Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes. Journal of the American Chemical Society 132(40): 13997-13999.

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https://hdl.handle.net/10161/4045

Published Version (Please cite this version)

10.1021/ja1057407

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