jo7b00579_si_001.pdf (7.41 MB)
Catalytic Enantioselective Synthesis of 3,4-Unsubstituted Thiochromenes through Sulfa-Michael/Julia–Kocienski Olefination Cascade Reaction
journal contribution
posted on 2017-04-07, 00:00 authored by Amit Kumar Simlandy, Santanu MukherjeeA 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).