ChemInform Abstract: anti-Selective Aldol Reactions of Pentafluorosulfanylacetic Acid Esters with Aldehydes Mediated by Dicyclohexylchloroborane

Autor:	Günter Haufe, Anna Lena Dreier, Joseph S. Thrasher, Constantin G. Daniliuc, Florian W. Friese, Andrej V. Matsnev
Rok vydání:	2016
Předmět:	chemistry.chemical_compound chemistry Aldol reaction Acetic Acid Esters Organic chemistry General Medicine Nuclear magnetic resonance spectroscopy Asymmetric induction Triethylamine
Zdroj:	ChemInform. 47
ISSN:	0931-7597
DOI:	10.1002/chin.201629069
Popis:	Aldol 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.
Databáze:	OpenAIRE
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