Journal
ORGANIC LETTERS
Volume 18, Issue 4, Pages 880-883Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00273
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Funding
- National Natural Science Foundation of China [21572262, U1403301, 21372255]
- YCSTTC Project of Xinjiang Uygur Autonomous Region [2013711017]
- Recruitment Program of Global Experts (Xinjiang Program)
- Director Foundation of XTIPC [2015RC014]
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Coupling of alpha-ketoesters with imines initiated by diethyl phosphite in the presence of alkaline metal hexamethyldisilazides is reported. Base-promoted addition of diethyl phosphite to a-ketoesters, followed by [1,2]-phosphonate/phosphate rearrangement, generates alpha-phosphonyloxy enolates that are subsequently intercepted by imines. The use of suitable azomethine coupling partners allows selective construction of syn-alpha-hydroxy-beta-amino acid derivatives or trans-aziridine-2-carboxylates in high yields with excellent diastereoselectivities.
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