Journal
ORGANIC LETTERS
Volume 21, Issue 3, Pages 593-597Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03436
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Funding
- National Science Foundation of China [21472151, 21822303, 21772020]
- Specialized Research Fund for the Doctoral Program of Higher Education [20110182110006]
- Fundamental Research Funds for the Central Universities (Chongqing University) [2018CDXZ0002, 2018CDPTCG0001/4]
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An efficient method for preparing highly functionalized chiral nonspiro-phosphonylpyrazolines via an asymmetric formal 1,3-dipolar cycloaddition reaction of alpha-diazomethylphosphonate with activated, acyclic alpha,beta-unsaturated ketones, bearing an additional nitrile electron-withdrawing group, has been developed, utilizing an in situ generated chiral silver phosphate catalyst, affording excellent stereoselectivities (up to 98% ee, 99:1 dr) and yields (up to 95%). A stepwise mechanism is proposed based upon density functional M11 calculations.D
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