Enantioselective organocatalyzed functionalization of benzothiophene and thiophenecarbaldehyde derivatives

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• 作者：Francesco Secci^a ; ^{fsecci@unica.it} ; Enzo Cadoni^a ; ^{ecadoni@unica.it} ; Claudia Fattuoni^a ; Angelo Frongia^a ; Giuseppe Bruno^b ; Francesco Nicolò ; ^b
• 关键词：Organocatalysis ; Enantioselectivity ; Regiochemistry ; Aldol reactions ; Benzothiophene
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：17 June, 2012
• 卷：68
• 期：24
• 页码：4773-4781
• 文件大小：3675 K

摘要

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 掳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.