Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 21, Pages 14250-14289Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02271
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Funding
- National Institutes of Health [GM R35 127010]
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A Lewis base catalyzed, enantioselective sulfenocyclization of alkenes to afford [6,6]spiroketals has been developed with excellent yields and enantioselectivities. The method allows for rapid formation of highly substituted spiroketals using a chiral Lewis base catalyst and electrophilic sulfur source.
A Lewis base catalyzed, enantioselective sulfenocyclization of alkenes to afford [6,6]spiroketals has been developed. The method uses a chiral Lewis base catalyst with an electrophilic sulfur source to generate enantioenriched thiiranium ion with alkenes. Upon formation, the thiiranium ion is subsequently captured in a cascade-type reaction, wherein a ketone oxygen serves as the nucleophile to open the thiiranium ion and an alcohol provides the secondary cyclization to form biorelevant spiroketals. A variety of electron-rich and electron-neutral E-substituted styrenes form the desired spiroketals in good yields with excellent enantio-and diastereoselectivities. Alkyl-substituted and terminal alkenes participate in the cascade reaction, but with a limited scope compared to the styrenyl substrates. This method allows for rapid formation of highly substituted spiroketals in good yield and excellent enantioselectivity.
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