Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes
Publication type: Journal Article
Publication date: 2017-05-16
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
28508653
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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.
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GOST
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Tekkam S., Finn M. Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes // Organic Letters. 2017. Vol. 19. No. 11. pp. 2833-2836.
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Tekkam S., Finn M. Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes // Organic Letters. 2017. Vol. 19. No. 11. pp. 2833-2836.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.7b00990
UR - https://doi.org/10.1021/acs.orglett.7b00990
TI - Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes
T2 - Organic Letters
AU - Tekkam, Srinivas
AU - Finn, M.G.
PY - 2017
DA - 2017/05/16
PB - American Chemical Society (ACS)
SP - 2833-2836
IS - 11
VL - 19
PMID - 28508653
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Tekkam,
author = {Srinivas Tekkam and M.G. Finn},
title = {Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes},
journal = {Organic Letters},
year = {2017},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.orglett.7b00990},
number = {11},
pages = {2833--2836},
doi = {10.1021/acs.orglett.7b00990}
}
Cite this
MLA
Copy
Tekkam, Srinivas, and M.G. Finn. “Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes.” Organic Letters, vol. 19, no. 11, May. 2017, pp. 2833-2836. https://doi.org/10.1021/acs.orglett.7b00990.
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