Herein we report a study on the enantioselective organocatalyzed cross-aldol reaction of 1-benzothiophene and thiophenecarbaldehydes with different ketones. The reactions were conducted at 0 degrees C or room temperature to afford the corresponding adducts in high yields and good to excellent ee using different organocatalysts. Interestingly, using (S)-pyrrolidine tetrazole and acetoxyacetone an inversion of the aldol regiochemistry was observed.
Enantioselective organocatalyzed functionalization of benzothiophene and thiophenecarbaldehyde derivatives
SECCI, FRANCESCO;CADONI, ENZO;FATTUONI, CLAUDIA;FRONGIA, ANGELO;
2012-01-01
Abstract
Herein we report a study on the enantioselective organocatalyzed cross-aldol reaction of 1-benzothiophene and thiophenecarbaldehydes with different ketones. The reactions were conducted at 0 degrees C or room temperature to afford the corresponding adducts in high yields and good to excellent ee using different organocatalysts. Interestingly, using (S)-pyrrolidine tetrazole and acetoxyacetone an inversion of the aldol regiochemistry was observed.
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