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An Expeditious Route to trans ‐Configured Tetrahydrothiophenes Enabled by Fe(OTf) 3 ‐Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters
Author(s) -
Matsumoto Yohei,
Nakatake Daiki,
Yazaki Ryo,
Ohshima Takashi
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800957
Subject(s) - cycloaddition , catalysis , yield (engineering) , chemistry , acceptor , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , physics , metallurgy , condensed matter physics
Abstract 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.