Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Catalytic Enantioselective Synthesis of 3,4-Unsubstituted Thiochromenes through Sulfa-Michael/Julia–Kocienski Olefination Cascade Reaction

Catalytic Enantioselective Synthesis of 3,4-Unsubstituted Thiochromenes through Sulfa-Michael/Julia–Kocienski Olefination Cascade Reaction
Amit Kumar Simlandy, Santanu Mukherjee
A highly enantioselective cascade sulfa-Michael/Julia–Kocienski olefination reaction between 2-mercaptobenzaldehydes and β-substituted vinyl PT-sulfones has been realized for the synthesis of 3,4-unsubstituted 2H-thiochromenes. This reaction, catalyzed by diphenylprolinol TMS ether, proceeds through an aromatic iminium intermediate and furnishes a wide range of 2-substiuted 2H-thiochromenes with excellent enantioselectivities (up to 99:1 er).

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00579

DOI: 10.1021/acs.joc.7b00579

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