Asymmetric Organocatalytic Stepwise [2+2] Entry to Tetra‐Substituted Heterodimeric and Homochiral Cyclobutanes. Issue 27 (24th May 2016)

• Record Type: Journal Article
• Authors: Nielsen, Alex J.; Jenkins, Hilary A.; McNulty, James
• Is Part Of: Chemistry. Volume 22:Issue 27(2016)
• Page Start: 9111
• Page End: 9115
• Publication Date: 2016-05-24
• Subjects: asymmetric synthesis -- cyclobutanes -- lignan dimers -- organocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201601842
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: An asymmetric synthesis of tetra‐substituted cyclobutanes involving an organocatalytic, stepwise [2+2]‐cycloaddition is described. The secondary‐amine‐catalyzed method allows for the hetero‐dimerization of two different cinnamic‐acid‐derived sub‐units, opening a novel one‐step assembly to densely functionalized, head‐to‐tail coupled dimeric cyclobutanes in high enantiomeric excess. A series of selective synthetic interconversions in these sensitive cycloadducts is also described. Abstract : Head‐to‐tail approach : An asymmetric synthesis of tetra‐substituted cyclobutanes involving an organocatalytic, stepwise [2+2]‐cycloaddition is described. The secondary‐amine‐catalyzed method allows for the hetero‐dimerization of two different cinnamic acid‐derived sub‐units, opening a novel one‐step assembly to densely functionalized, head‐to‐tail coupled dimeric cyclobutanes in high enantiomeric excess. A series of selective synthetic interconversions in these sensitive cycloadducts is also described.