The first preparation of (1S,5R)-(−)- and (1R,5S)-(+)-7-phenyl-3-borabicyclo[3.3.1]non-6-enes and their application for synthesis of chiral cyclohexene derivatives

(1S,5R)-(−)- and (1R,5S)-(+)-7-phenyl-3-borabicyclo[3.3.1]non-6-enes of 97–98% de that differed only by the location of the double bond were prepared by the resolution of diastereomeric intramolecular chelates with l- and d-prolinol. Deboronation of chiral bicyclic boranes obtained was used for synthesis of optically active 3,5-dimethyl- and 3,5-dihydroxymethyl-1-phenylcyclohexenes.

Graphical abstract(1S,5R)-(−)- and (1R,5S)-(+)-7-phenyl-3-borabicyclo[3.3.1]non-6-enes that differed only by the location of the double bond were prepared by the resolution of diastereomeric intramolecular chelates with l- and d-prolinol.Figure optionsDownload full-size imageDownload as PowerPoint slide