ol6b00136_si_002.cif (1.97 MB)
Anti-Selective Aldol Reactions of Pentafluorosulfanylacetic Acid Esters with Aldehydes Mediated by Dicyclohexylchloroborane
dataset
posted on 2016-02-24, 00:00 authored by Florian
W. Friese, Anna-Lena Dreier, Andrej V. Matsnev, Constantin G. Daniliuc, Joseph S. Thrasher, Günter HaufeAldol
reactions of pentafluorosulfanyl (SF5)-substituted
acetic acid esters with both aromatic and aliphatic aldehydes proceeded
with excellent anti-diastereoselectivity and good
to high yields using dicyclohexylchloroborane/triethylamine. This
methodology enabled the synthesis of hitherto unknown α-SF5-β-hydroxy esters. Using a norephedrine-based auxiliary,
high asymmetric induction was observed. The stereochemistry of products
was assigned by NMR spectroscopy and proved by X-ray diffraction analysis.
The intermediate enolate was identified as a highly unstable species.