期刊
ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 3, 期 4, 页码 458-461出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201300211
关键词
-fluoro--ketophosphonates; asymmetric synthesis; Michael addition; organofluorine; phosphate mimetics
资金
- National University of Singapore [R-143-000-469-112]
- Ministry of Education (MOE) of Singapore [R-143-000-494-112]
- GSK-EDB [R-143-000-491-592]
Fluorinated phosphonates are excellent surrogates of phosphates, outperforming the latter in terms of hydrolytic stability in biological systems while retaining similar activities. However, methods for preparing chiral fluorinated phosphonates are very limited. In this report, racemic -fluoro--ketophosphonates were used in stereoselective Michael addition to nitroalkenes promoted by trifunctional thiourea organocatalyst. Highly functionalised -fluoro--keto--nitrophosphonates were obtained in high yields of 84-99% with excellent stereochemical control (96-99% ee and 3:1-34:1 d.r.).
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