Chiral Sulfide Catalysis for Desymmetrizing Enantioselective Chlorination

A chiral sulfide catalyzed the desymmetrizing enantioselective chlorination of various aryl‐tethered diolefins and diaryl‐tethered olefins to afford teralins and tricyclic hexahydrophenalene derivatives, respectively, bearing multiple stereogenic centers. In contrast, the tertiary amine catalyst (DHQD)₂PHAL led to a diastereomeric product. The products could be transformed into diverse compounds such as spiro‐N‐heterocycles.

Abstract

An unprecendented chiral sulfide catalyzed desymmetrizing enantioselective chlorination is disclosed. Various aryl‐tethered diolefins and diaryl‐tethered olefins afforded teralins and tricyclic hexahydrophenalene derivatives, respectively, bearing multiple stereogenic centers in high yields with excellent enantio‐ and diastereoselectivities. In contrast, the tertiary amine catalyst (DHQD)₂PHAL led to a diastereomeric product. The products could be transformed into a variety of compounds, such as spiro‐N‐heterocycles.

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