期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2016, 期 6, 页码 1165-1172出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501449
关键词
Synthetic methods; Domino reactions; Diastereoselectivity; Spiro compounds; Nitrogen heterocycles
资金
- National Natural Science Foundation of China (NSFC) [20972070, 21121002]
- National Basic research Program of China (973 program) [2010CB833300]
- Program for New Century Excellent Talents in University [NCET-11-0265]
- Key Laboratory of Elemento-Organic Chemistry
The application of readily available optically active 4-substituted 5-nitropentan-2-ones as chiral building blocks in the stereocontrolled construction of spiro-pyrazolone scaffolds was investigated. In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (1 equiv.) optically active 4-substituted 5-nitropentan-4-ones exhibited excellent chiral inducing abilities in the diastereoselective cascade Michael/aldol reaction with a wide range of unsaturated pyrazolones to generate the corresponding biologically significant spiro-pyrazolone derivatives with five contiguous stereocenters in acceptable to good yield with high levels of diastereoselectivity.
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