Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 5, Pages 1206-1208Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja110500m
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Funding
- Robert A. Welch Foundation [I-1748]
- W.W. Caruth, Jr., Endowed Scholarship
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The first Pd-catalyzed enantioselective [2,3]-rearrangement of allylic amine N-oxides is described, which formally represents an asymmetric Meisenheimer rearrangement. The mild reaction conditions enable the synthesis of chiral nonracemic aliphatic allylic alcohol derivatives with reactive functional groups. On the basis of preliminary studies, a cyclization-mediated mechanism is proposed.
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