Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 11, Pages 1854-1858Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600059
Keywords
allylation; allylic amines; nitroacetates; palladium; stereospecificity
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Funding
- National Natural Science Foundation of China [21472178, 21232007]
- National Key Basic Research Program of China [2014CB931800]
- Natural Science Foundation of Anhui Province of China [1408085MB24]
- Innovative Program of Development Foundation of Hefei Center for Physical Science and Technology [2014FXCX002]
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An unprecedented stereospecific allylation reaction of nitroacetates with enantioenriched primary allylic amines has been developed. A range of nitroacetates smoothly underwent allylation with enantioenriched primary allylic amines in the presence of a palladium catalyst and boric acid followed by one-pot decarboxylation to afford structurally diverse homoallylic nitro compounds in good to excellent yields with excellent retention of configuration. On the other hand, the allylation followed by denitronation provided a facile synthetic route to optically active -chiral ,-unsaturated esters.
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