Organic Letters
Organic Letters
5 years ago

Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes

Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes
M. G. Finn, Srinivas Tekkam
Furfuryl carbamates are labile and require care to be accessed by activating furfuryl alcohols. An alternative oxanorbornadiene (OND)-based strategy is presented for the preparation of 5-R-substituted furfuryl carbamates via the reactions of amines with intermediate OND carbonates. The resulting OND carbamates, which are stable for several months, undergo thiol mediated retro-Diels–Alder reaction to deliver the desired furfuryl carbamates in a single flask. Conditions for the selective hydrolysis of furfuryl carbamates in the presence of tert-butyloxycarbonyl (Boc) groups were identified, and it was shown that furfuryl carbamates can be used as a prodrug handle.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00990

DOI: 10.1021/acs.orglett.7b00990

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