An efficient application of aryl and hetaryl thioketones as dienophiles in the enantioselective thia‐Diels–Alder reaction was explored for the first time. It was found that thioketones could serve as useful heterodienophiles in aminocatalytic, trienamine‐mediated [4+2] cycloadditions with 2,4‐dienals. This enantioselective approach (up to 99:1 er) was efficiently promoted by diarylprolinol silyl ethers and led to new types of potentially relevant 5,6‐dihydro‐2H‐thiopyrans.
The development of the unprecedented ortho-regioselective inverse-electron-demand hetero-Diels-Alder (IEDHDA) reaction is described. It has been demonstrated that by proper choice of reactants and reaction conditions the inverse-electron-demand hetero-Diels-Alder cycloaddition can be realized with unprecedented regioselectivity arising from the reaction between the terminal carbon atom of the dienophile and the heteroatom of the heterodiene.
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