Li, Hongming; Wang, Yi; Tang, Liang; Deng, Li published the artcile< Highly Enantioselective Conjugate Addition of Malonate and å°?Ketoester to Nitroalkenes: Asymmetric C-C Bond Formation with New Bifunctional Organic Catalysts Based on Cinchona Alkaloids>, Synthetic Route of 112-63-0, the main research area is nitroester enantioselective preparation; gamma nitroester enantioselective prepare; hydroxyquinidine hydroxyquinuclidine catalyst Michael addition malonate acetoacetate nitroalkene; enantioselective Michael addition malonate nitroalkene hydroxyquinidine hydroxyquinuclidine catalyst; aryl heteroaryl alkyl nitroalkene enantioselective Michael addition malonate hydroxyquinidine; hydroxyquinine aryl heteroaryl alkyl nitroalkene enantioselective Michael addition malonate; rate dependence enantioselective Michael addition nitroalkene malonate hydroxyquinine; conjugate addition malonate ketoester nitroalkene cinchona alkaloid bifunctional catalyst; asym bond formation bifunctional organic catalyst cinchona alkaloid.
Quinine and quinidine derivatives such as I and II are prepared; in the presence of I or II, nitroalkanes (E)-RCH:CHNO2 (R = Ph, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-MeC6H4, 4-Me2CHC6H4, 4-MeOC6H4, 3-MeC6H4, 2-MeC6H4, 2-FC6H4, 2-O2NC6H4, 1-naphthyl, 2-thienyl, 2-furyl, 3-pyridinyl, BuCH2, Me2CHCH2, c-C6H11) undergo enantioselective addition reactions with di-Me malonate to provide either enantiomer of the nitroesters O2NCH2CHRCH(CO2Me)2 (III) (R = Ph, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-MeC6H4, 4-Me2CHC6H4, 4-MeOC6H4, 3-MeC6H4, 2-MeC6H4, 2-FC6H4, 2-O2NC6H4, 1-naphthyl, 2-thienyl, 2-furyl, 3-pyridinyl, BuCH2, Me2CHCH2, c-C6H11) in 71-99% yields and in 91-97% ee. Aryl, heteroaryl, and alkyl-substituted nitroalkenes give conjugate addition products in high yields and enantioselectivities. Cinchona alkaloids with a 6′-hydroxy group yield III with much higher enantioselectivities than those bearing 6′-methoxy groups; etherification of the secondary alc. of alkaloids such as I or II alters the enantioselectivity and yield of Michael addition reactions catalyzed by them minimally. The enantioselectivity of Michael additions catalyzed by I and II is attributed to bifunctional catalysis using both the 6′-hydroxy group and the quinuclidine amine moiety. Kinetic studies on the addition of di-Me malonate to III (R = Ph) in the presence of I indicate that the rate of reaction is first order in nitroalkene, di-Me malonate, and catalyst. Et acetoacetate undergoes conjugate addition to trans-å°?nitrostyrene III (R = Ph) to yield çº?nitro ester O2NCH2CHPhCHAcCO2Et as a 1:1 mixture of diastereomers at the ä¼?acetyl ester in 93% yield; both diastereomers are isolated in 91% ee.
Journal of the American Chemical Society published new progress about 1,3-Dicarbonyl compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Synthetic Route of 112-63-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics