期刊
ACS CATALYSIS
卷 12, 期 15, 页码 9690-9697出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c02537
关键词
1,3-dienes; rhodium catalysis; pi-allyl complex; amino oxygenation; 1,2-amino alcohols; three-component reactions; dioxazolones
资金
- NIGMS [GM80442]
- Alexander von Humboldt Foundation
- National Institutes Of Health of the National Institutes of Health [S10OD026749]
In this study, a modular strategy for diastereoselective 3,4-amino oxygenation and diamination of 1,3-dienes using different O- and N-nucleophiles with readily available 3-substituted 1,4,2-dioxazolones has been reported. The use of hexafluoroisopropanol as a non-nucleophilic solvent allows for the use of diverse nucleophiles and greatly expands the scope of the transformation.
We herein report a modular strategy, which enables Rh(III)-catalyzed diastereoselective 3,4-amino oxygenation and diamination of 1,3-dienes using different O- and N-nucleophiles in combination with readily available 3-substituted 1,4,2-dioxazolones (78 examples, 37-91% yield). Previous attempts to functionalize the internal double bond rested on the use of plain alcoholic solvents as nucleophilic coupling partners thus dramatically limiting the scope of this transformation. We have now identified hexafluoroisopropanol as a non-nucleophilic solvent that allows the use of diverse nucleophiles and greatly expands the scope, including an unprecedented amino hydroxylation to selectively install valuable, unprotected ss-amino alcohols across 1,3-dienes. Moreover, various elaborate alcohols prove to be compatible providing unique access to complex organic molecules. Finally, this method is employed in a series of intramolecular reactions to deliver valuable nitrogen heterocycles as well as gamma- and delta-lactones.
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