Work

Practical Access to Trisubstituted Morita‐Baylis‐Hillman‐Type Products Through Copper‐Catalyzed Reductive Aldol Reactions of Alkynones

Year: 2024

Type: article

Abstract: We 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.

Source: Asian Journal of Organic Chemistry

DOI: 10.1002/ajoc.202400422

Authors: Stephan Scheeff, Pauline Chiu

Institutions: State Key Laboratory of Synthetic Chemistry, University of Hong Kong

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,840

Funder: University of Hong Kong