Organocatalytic enantioselective Michael addition of 2,4-pentandione to nitroalkenes promoted by bifunctional thioureas with central and axial chiral elements.
Two novel bifunctional amine-thiourea organocatalysts 1 and 2, which both bear central and axial chiral elements, have been developed to promote enantioselective Michael reaction between 1,3-dicarbonyl compounds and nitro olefins. The catalyst 2 afforded the desired products with good levels of enantioselectivity (up to 96% ee), showing clearly that two chiral elements of 2 are matched, and enhance the stereochemical control.
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China.
Fang-Zhi
FZ
Peng
Zhi-Hui
ZH
Shao
Bao-Min
BM
Fan
He
H
Song
Gan-Peng
GP
Li
Hong-Bin
HB
Zhang
D000475:Alkenes / Q000737:chemistry*; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000737:chemistry*; D010422:Pentanones / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry*
D000475:Alkenes; D017672:Nitrogen Compounds; D010422:Pentanones; D013457:Sulfur Compounds; C008790:acetylacetone