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Copper-Catalyzed Aqueous N-O Bond Cleavage of 2-Oxa-3-Azabicyclo Compounds to Cyclic cis-1,4-Amino Alcohols.

ChemSusChem

Yasukawa N, Miki Y, Kuwata M, Sajiki H, Sawama Y.
PMID: 32820617
ChemSusChem. 2020 Nov 06;13(21):5632-5637. doi: 10.1002/cssc.202001739. Epub 2020 Sep 09.

The N-O bond cleavage of 2-oxa-3-azabicyclo substrates, which are readily prepared by the hetero Diels-Alder reaction between nitroso dienophiles and cyclic 1,3-dienes, was effectively catalyzed by heterogeneous copper-on-carbon (Cu/C) under aqueous conditions to give the corresponding cyclic cis-1,4-amino alcohol...

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