Journal
CHEMICAL COMMUNICATIONS
Volume 49, Issue 60, Pages 6800-6802Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc44117b
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Funding
- ACS PRF
- NSF CAREER Award
- University of Washington
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A palladium-catalyzed hydroamination reaction is the key step in a stereoselective synthesis of 2,5-disubstituted and 2,3,5-trisubsituted morpholines from carbamate-protected aziridines. Aziridines are selectively attacked at the more substituted position by unsaturated alcohol nucleophiles using Lewis acid catalysts. Palladium-catalyzed hydroamination of the resulting aminoalkenes gives morpholines as a single diastereomer in excellent yield.
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