TY - JOUR
T1 - An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters
AU - Matsumoto, Yohei
AU - Nakatake, Daiki
AU - Yazaki, Ryo
AU - Ohshima, Takashi
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant Number JP15H05846 in Middle Molecular Strategy, JP16H01032 in Precisely Designed Catalysts with Customized Scaffolding and Platform for Drug Discovery, Informatics, and Structural Life Science from MEXT. Drs. Kazuteru Usui and Yasu-fumi Fuchi are gratefully acknowledged for analytical measurement assistance. We are grateful to Prof. Hirai’s group for the use of polarimeter.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/4/20
Y1 - 2018/4/20
N2 - 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.
AB - 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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U2 - 10.1002/chem.201800957
DO - 10.1002/chem.201800957
M3 - Article
C2 - 29488258
AN - SCOPUS:85044295635
SN - 0947-6539
VL - 24
SP - 6062
EP - 6066
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 23
ER -