A highly practical approach to chiral homoallylic–homopropargylic amines via aza-Barbier reaction

Stereocontrolled Addition of Scrambling ortho-Sulfinyl Carbanions: Easy Access to Homopropargylamines and α-Allenylamines

“…Related to the present work, Yin and co-workers have described an asymmetric copper-catalyzed alkynylogous aldol addition of propargyl esters to aldehydes, giving access to the corresponding enantio-enriched α-allenyl alcohols . Regarding the preparation of homopropargyl amines, the most frequently employed procedures rely on the use of Schiff bases in the presence of propargyl or allenyl moieties . In this regard, earlier this year, Qiu and Hu reported an enantioselective multicomponent strategy, enabling the preparation of optically active homopropargyl amines.…”

Asymmetric Multicomponent Reactions for Efficient Construction of Homopropargyl Amine Carboxylic Esters

“…Enantiomerically pure homopropargyl amines are versatile building blocks for the synthesis of many bioactive compounds and natural products, , such as indolizidine 209B and hederacine A. , As such, developing enantioselective synthetic methods for these compounds is of great interest to the synthetic community . A traditionally synthetic approach toward α-branched homopropargyl amines is enantioselective propargylation of Schiff bases with various propargyl or allenyl metal reagents (Scheme a), and considerable efforts have been made to develop catalytically asymmetric methods, relying on developing novel chiral metal complexes . However, these propargylation reactions that involve the use of stoichiometrically synthesized or pregenerated propargyl or allenyl metals would strongly limit the chemical and functional diversity of the final products.…”