Institute and State Key Laboratory of Elemento Organic Chemistry

Tianjin, China

Institute and State Key Laboratory of Elemento Organic Chemistry

Tianjin, China
SEARCH FILTERS
Time filter
Source Type

Sun J.,Institute and State Key Laboratory of Elemento Organic Chemistry | Sun J.,Nankai University | Jiang C.,Institute and State Key Laboratory of Elemento Organic Chemistry | Jiang C.,Nankai University | And 2 more authors.
European Journal of Organic Chemistry | Year: 2016

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. Optically active 4-substituted 5-nitropentan-2-ones proved valuable chiral building blocks in the stereocontrolled construction of spiro-pyrazolone scaffolds. A range of spiro-pyrazolones were synthesized in good yields with high levels of diastereo- and enantioselectivity through a base-mediated cascade Michael/aldol reaction between 4-substituted 5-nitropentan-2-ones and unsaturated pyrazolones. © Copyright 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Cui L.-Y.,Institute and State Key Laboratory of Elemento Organic Chemistry | Cui L.-Y.,Nankai University | Wang Y.-H.,Institute and State Key Laboratory of Elemento Organic Chemistry | Wang Y.-H.,Nankai University | And 6 more authors.
RSC Advances | Year: 2015

An efficient approach for the stereocontrolled construction of 3H-furo[3,4-b]chromen-1(9H)-one skeleton has been successfully developed through a sequential Michael addition/intramolecular dehydration strategy. The Michael addition of tetronic acid to 2-((E)-2-nitrovinyl)phenols catalyzed by a bifunctional squaramide derived from l-tert-leucine, and the subsequent intramolecular dehydration promoted by concentrated sulfuric acid, proceed smoothly to give the corresponding pharmaceutically valuable 3H-furo[3,4-b]chromen-1(9H)-ones in acceptable yields with 79-97% ee. © The Royal Society of Chemistry.

Loading Institute and State Key Laboratory of Elemento Organic Chemistry collaborators
Loading Institute and State Key Laboratory of Elemento Organic Chemistry collaborators