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.
Peng
Fang-Zhi
FZ
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China.
Shao
Zhi-Hui
ZH
Fan
Bao-Min
BM
Song
He
H
Li
Gan-Peng
GP
Zhang
Hong-Bin
HB
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