10.1021/acs.orglett.6b00136.s002

<i>Anti</i>-Selective Aldol Reactions of Pentafluorosulfanylacetic Acid Esters with Aldehydes Mediated by Dicyclohexylchloroborane

Abstract

Aldol reactions of pentafluorosulfanyl (SF<sub>5</sub>)-substituted acetic acid esters with both aromatic and aliphatic aldehydes proceeded with excellent <i>anti</i>-diastereoselectivity and good to high yields using dicyclohexylchloroborane/triethylamine. This methodology enabled the synthesis of hitherto unknown α-SF<sub>5</sub>-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

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oai:figshare.com:article/2746282Last time updated on 2/12/2018

This paper was published in FigShare.

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