AI Article Synopsis
- The study demonstrates the use of visible light for carbene-transfer reactions involving diazoalkanes and cyclooctatetraene, leading to high-yield production of cyclopropanes with favorable stereoselectivity.
- This photochemical method outperforms traditional metal-catalyzed cyclopropanation processes, offering new opportunities for synthesizing valuable chemicals.
- The resulting cyclopropane structure aids in avoiding 6π electrocyclization and allows for targeted functionalization of the all-cis triene in further cycloaddition reactions.
Article Abstract
We report on the use of visible light to conduct carbene-transfer reactions of donor/acceptor diazoalkanes with cyclooctatetraene and polyunsaturated carbocycles to give the corresponding cyclopropanes in excellent yields with excellent stereoselectivities. This photochemical protocol proved to be superior to conventional metal-catalyzed cyclopropanation reactions and now provides platform chemicals containing a cyclic conjugated all-cis triene. The cyclopropane is an important structural feature to prevent 6π electrocyclization. Instead, the triene moiety can now be selectively functionalized in cycloaddition reactions.
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| http://dx.doi.org/10.1021/acs.orglett.0c01734 | DOI Listing |
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