Asymmetric Organocatalytic 1,4‐Addition Reactions Starting from Enals with gem‐Difluoroalkyl Side Chains

Abstract

gem‐Difluoroenals are excellent substrates for asymmetric organocatalytic 1,4‐additions of thiols and anilines. By using diarylsilylprolinol ether as a catalyst, good to excellent yields with ee values in the same range (up to 98 %) were obtained. The CF2R group strongly activates the enals towards these organocatalytic additions.

A Concise Enantioselective Synthesis of Fluorinated Pyrazolo-Piperidine GSK3901383A Enabled by an Organocatalytic Aza-Michael Addition

“…The organocatalytic aza-Michael reaction is a powerful transformation for the synthesis of bioactive molecules . Although pyrazoles have been demonstrated as suitable N–H nucleophiles, considerably less attention has been paid to the use of fluorinated α,β-unsaturated acceptors . We envisioned that an extension of this methodology using a suitable organocatalyst had the potential to succeed.…”