A concise one-pot route for the synthesis of 2,3-dihydroisoxazoles via a dual gold-iron catalysis has been devised. The method, based on the addition of binucleophilic protected hydroxylamine to propargylic alcohols, enables a one-pot, highly selective synthesis of these heterocycles (10 examples, up to 86% yield).

[reaction: see text] Anti alpha-amino-homopropargylic alcohols are prepared by addition of metallated propargylic amines to aldehydes. Among the four organometallic (LI, Zn, Ti, Cu) derivatives used, the most effective are the copper reagents.

SummaryThis personal account summarizes our recent developments in gold-catalyzed direct substitutions on propargylic (allylic, benzylic) alcohols, with various nucleophiles (and bi-nucleophiles) based on the σ- and/or π-acidity of gold(III) complexes. Synthetic developments are also briefly described.