Chemistry - A European Journal p. 6062 - 6066 (2018)
Update date:2022-08-04
Topics: Catalyzed [3+2] Cycloaddition Route Expeditious
Matsumoto, Yohei
Nakatake, Daiki
Yazaki, Ryo
Ohshima, Takashi
A synthetic route to trans-configured tetrahydrothiophenes (THTs) through Fe(OTf)3-promoted [3+2] cycloaddition of donor–acceptor cyclopropanes with thionoesters was developed. The cycloaddition proceeded in high yield with high diastereoselectivity, affording transient α-alkoxy THTs. Not only aromatic and aliphatic thionoesters, but also thionolactone were applicable to the present iron catalysis. Further transformation of the S,O-ketal functionality of the product was achieved in a highly trans diastereoselective manner. Moreover, the utility of our methodology was clearly demonstrated by the synthesis of enantioenriched trans-configured THTs.
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