Noyori's Ts-DPEN ligand: an efficient bifunctional primary amine-based organocatalyst in enantio- and diastereoselective Michael addition of 1,3-dicarbonyl indane compounds to nitroolefins
Noyori's Ts-DPEN ligand bearing an amino sulfonamide moiety and with a primary amino group on a chiral scaffold was found to be a simple and efficient bifunctional organocatalyst for the asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroolefins, which gave highly functional Michael adduct with quaternary stereocenters in good enantioselectivities (up to 84%ee) and dr (up to 5.7:1 dr).
Simple primary β-amino alcohols as organocatalysts for the asymmetric Michael addition of β-keto esters to nitroalkenes
Simple primary β-amino alcohols act as an efficient organocatalysts in the asymmetric Michael addition of β-keto esters with nitroalkenes affording highly pure chiral Michael adducts. Also, both enantiomers of the adducts were obtained, depending on the specific catalyst used and reaction temperature.
Amino amide organocatalysts for asymmetric michael addition of β-Keto esters with β-nitroolefins
Asymmetric Michael addition of β-keto esters with trans-β-nitroolefins using chiral amino amide organocatalyst was tried and afforded synthetically useful chiral Michael adducts in both excellent chemical yields (up to 99%) and stereoselectivities (up to dr. 99:1, up to 98% ee).
Asymmetric Michael addition mediated by novel cinchona alkaloid-derived bifunctional catalysts containing sulfonamides
(Chemical Equation Presented) Novel cinchona alkaloid-derived bifunctional organocatalysts containing sulfonamide groups were utilized to promote Michael addition of bicyclic α-substituted β-ketoesters to nitroolefins. The desired Michael adducts with all
Luo, Jie,Xu, Li-Wen,Hay, Robyn Aik Siew,Lu, Yixin
supporting information; experimental part
p. 437 - 440
(2009/07/25)
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