Access to Thiophene and 1H-Pyrrole via Amine-Initiated (3+2) Annulation and Aromatization Cascade Reaction of beta '-Acetoxy Allenoate and 1,2-Bisnucleophile

作者：Ni, Chunjie; Wang, MingLi; Tong, Xiaofeng^*

来源：Organic Letters, 2016, 18(9): 2240-2243.

DOI：10.1021/acs.orglett.6b00874

• ONE-POT SYNTHESIS
• ENANTIOSELECTIVE 4+1 ANNULATIONS
• HIGHLY SUBSTITUTED 3-PYRROLINES
• TETRASUBSTITUTED THIOPHENES
• FACILE SYNTHESIS
• S-ALKENYLATION
• DERIVATIVES
• 1,4-DITHIANE-2,5-DIOL
• SULFIDE
• 2-(ACETOXYMETHYL)BUTA-2,3-DIENOATE

The amine-catalyzed cascade (3 + 2) annulation and aromatization sequence between beta'-acetoxy allenoates and 1,2-bisnucleophiles has been developed. When 1,4-dithane-2,5-diol is used as the bisnucleophile partner, the corresponding reaction affords fully substituted thiophene-2-carbaldehyde, which might proceed via the amine-catalyzed (3 + 2) annulation and subsequent oxidative aromatization. The reaction protocol is also applicable to a 2-tosylamino-carbonyl bisnucleophile, wherein the (3 + 2) annulation is followed by 1,2-elimination of a tosyl group and isomerization to give a 1H-pyrrole product.

• 出版日期2016-5-6
• 单位华东理工大学; 常州大学