Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives

Jian Qiang Huang; Zackaria Nairoukh; Ilan Marek

doi:10.1039/C8OB00067K

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Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives†

Jian Qiang Huang,^a Zackaria Nairoukh^a and Ilan Marek

*^a

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* Corresponding authors

^a The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, 32000, Israel
E-mail: chilanm@technion.ac.il
Tel: +973-4-829-37-09

Abstract

A highly diastereoselective synthesis of tertiary α-fluoro carbonyl compounds is reported in only two chemical steps from a simple alkyne through the reaction of stereodefined fully substituted silyl ketene hemiaminal derivatives with Selectfluor.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/C8OB00067K
Article type: Communication
Submitted: 09 Jan 2018
Accepted: 16 Jan 2018
First published: 16 Jan 2018

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Org. Biomol. Chem., 2018,16, 1079-1082

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Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives

J. Q. Huang, Z. Nairoukh and I. Marek, Org. Biomol. Chem., 2018, 16, 1079 DOI: 10.1039/C8OB00067K

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Organic & Biomolecular Chemistry

Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives†

Abstract

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Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives

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