Practical access to trisubstituted Morita‐Baylis‐Hillman‐type products through copper‐catalyzed reductive aldol reactions of alkynones
October 31, 2024·
,·
0 min read
Stephan Scheeff
Pauline Chiu
Abstract
AbstractWe report a convenient and diastereoselective copper‐catalyzed reductive alkynone aldol addition to aldehydes, with pinacolborane as stoichiometric reductant, that results in the generation of densely functionalized, trisubstituted (Z)‐enone products analogous to Morita‐Baylis‐Hillman adducts. We demonstrate that the reaction proceeds via an allenolborate, which we have characterized by NMR spectroscopy. A range of aromatic and aliphatic aldehydes can be reductively coupled with various non‐terminal alkynones.
Type
Publication
Asian J. Org. Chem. 2024, 13, e202400422
Authors
Research Associate (Medicinal Chemistry)
Medicinal chemist designing novel antiviral and anticancer compounds. Researched nucleoside analogues at CUHK under Prof. Billy Ng since 2021, awarded Hong Kong Postdoctoral Fellowship 2022/2023. Enjoys exploring Hong Kong’s countryside and culture through photography.