Work

Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts

Year: 2015

Type: article

Abstract: The addition of an organic catalyst to the ketone moiety of a γ-mono-chloride substituted cyclobutenone destroys its stable, conjugated and nearly planar structure. The C-C bond in the resulting less stable anionic oxy-substituted non-planar intermediate is then activated. The breaking of one C-C single bond leads to a catalyst-bound intermediate that undergoes α-carbon selective reactions with azomethine imines to afford nitrogen-containing heterocyclic compounds with excellent diastereo- and enantio-selectivities. Our organocatalytic approach provides a new reaction pattern for C-C bond activation of cyclobutenones that is unavailable with transition metal catalysis. In addition, the present study with isothioureas as the organocatalysts expands the potential in using organocatalysts for C-C bond breaking and selective reactions.

Source: Chemical Science

DOI: 10.1039/c5sc01972a

Authors: Bao-Sheng Li, Yuhuang Wang, Zhichao Jin, Yonggui Robin Chi

Institutions: Nanyang Technological University, Guizhou University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond