Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: synthetic applications using thioesters
Articolo
Data di Pubblicazione:
1984
Citazione:
Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: synthetic applications using thioesters / C.M.A. Gennari, A. Bernardi, S. Cardani, C. Scolastico. - In: TETRAHEDRON. - ISSN 0040-4020. - 40:20(1984), pp. 4059-4065.
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. © 1984.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
C.M.A. Gennari, A. Bernardi, S. Cardani, C. Scolastico
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