Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: synthetic applications using thioesters |
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Authors: | Cesare Gennari Anna Bernardi Silvia Cardani Carlo Scolastico |
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Institution: | Istituto di Chimica Organica dell''Universitié Centro CNR Sost. Org. Nat., via G.Venezian 21, 20133 Milano Italy |
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Abstract: | A detailed Investigation of the enolization of phenyl thiopropionate with ethylenechloroboronate (ECB) and diisopropylethylamine (DPEA) and the subsequent aldol condensations of these enolates was conducted. Alkenyloxy dialkoxyboranes derived from thioesters were found to be stereoconvergent: both Z and E enolates give syn aldol condensation products. The thioester additions to chiral aldehydes were studied. Internal selectivity (syn) was usually very high, while the relative stereoselectivity ranged from poor to good, depending on the specific aldehyde used. The aldol products were transformed to known compounds for correlation. |
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