208242-73-3

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 1192-37-6 methylenecyclohexane 

Downstream Products

• 126214-08-2 methyl (S)-3-(1'-cyclohexenyl)-2-hydroxypropionate 
• 1402854-51-6 (1R,3S,4aS,8aS)-ethyl 4a-hydroxy-1-((E)-styryl)octahydro-1H-isochromene-3-carboxylate 

Relevant academic research and scientific papers

C2-symmetric copper(II) complexes as chiral lewis acids. Catalytic enantioselective carbonyl - Ene reactions with glyoxylate and pyruvate esters

The C2-symmetric complexes [Cu(S,S)-tert-butylbis(oxazolinyl)](SbF6)2 (2a), its bis(aquo) counterpart [Cu(S,S)-tert-butylbis(oxazolinyl)(H2O)2](SbF6)2 (4), and [Cu(S,S)-phenylbis(oxazolinyl)](OTf)2 (1c) have been shown to catalyze the enantioselective ene reaction between glyoxylate esters and various olefins. Monosubstituted, disubstituted, and trisubstituted olefins each react with ethyl glyoxylate in the presence of 0.2 - 10 mol % of catalysts 1, 2, and 4 to afford the ene products in good yield and enantioselectivity. Complex 2a has also been shown to catalyze the addition of 1,1-disubstituted olefins to methyl pyruvate in good yields (76-95%) and excellent enantioselectivies (≥98% ee). The synthetic utility of the glyoxylate - ene reaction was demonstrated by conversion of the resulting α-hydroxy ester into the corresponding methyl ester, free acid, Weinreb amide, and α-azido ester, all with no detectable racemization.

Enhanced reactivity and enantioselectivity in catalytic glyoxylate-ene reactions using chiral bis(oxazoline)-copper complex in an ionic liquid

An optimal hydrophobic ionic liquid was discovered as a solvent for highly enantioselective glyoxylate-ene reactions catalyzed by a chiral bis(oxazoline)-copper complex. The reactivity and stereoselectivity were highly dependent upon the property of the i

Enantioselective carbonyl-ene reactions catalyzed by chiral cationic dirhodium(II,III) carboxamidates

(Chemical Equation Presented) An enantioselective carbonyl-ene reaction of glyoxylate esters with 1,1-disubstituted alkenes catalyzed by chiral cationic dirhodium(II,III) carboxamidates is described. The paddlewheel dirhodium(II,III) carboxamidates having

Electrostatically immobilised BOX and PYBOX metal catalysts: application to ene reactions

Copper(I), copper(II) and scandium(III) triflate complexes of BOX and PYBOX ligands have been electrostatically immobilised on silica. The performance of the immobilised catalysts, in the two carbonyl-ene reactions studied, compares very well with that of

Enantioselective glyoxylate-ene reactions catalysed by (salen)chromium(III) complexes

An enantioselective carbonyl-ene reaction of alkyl glyoxylates with various 1,1-disubstituted olefins, catalysed by chiral (salen)Cr(III)BF4 complexes, has been studied. We found that a chromium complex bearing adamantyl substituents at the 3,3

Heterogeneous enantioselective catalyzed carbonyl- and imino-ene reactions using copper bis(oxazoline) zeolite Y

A recovery discovery: A simple pathway for the synthesis of α-hydroxy and α-amino carbonyl compounds with good yields and high enantioselection is provided by the first heterogeneously catalyzed enantioselective carbonyl-ene and imino-ene reactions. The c

Insoluble polystyrene-bound bis(oxazoline): Batch and continuous-flow heterogeneous enantioselective glyoxylate-ene reaction

The use of a new, insoluble polymer-bound bis(oxazoline) ligand (IPB-box) for the copper-catalyzed heterogeneous enantioselective glyoxylate-ene reaction is described. Good activity and ee values in the range 85-95% have been obtained during five to seven recycles, either in batch mode or under flow conditions, demonstrating also the recovery and reuse of the whole catalytically active copper complex.

Helical Chirality Control of Palladium Complexes That Bear a Tetrakis(phosphanyl)terphenyl Ligand: Application as Asymmetric Lewis Acid Catalysts

Both axial and helical chirality are generated by complexation of the novel tetrakis(phosphanyl)terphenyl (tetraphos) ligand to a metal center (see picture). The tropos nature of the ligand was confirmed, and enantiopure Pd complexes controlled by diamines were applied as asymmetric Lewis acid catalysts in carbonyl-ene reactions.

Quasi Solvent-Free Enantioselective Carbonyl-Ene Reaction with Extremely Low Catalyst Loading

Simply mixing the neat substrates and a small amount of the chiral catalyst (0.1-0.01 mol%) under nearly solvent-free conditions makes the enantioselective carbonyl-ene reaction of glyoxylate ester with a variety of olefins proceed smoothly to afford the

Dynamic asymmetric catalysis by diphenylphosphinoferrocene (DPPF)-nickel complexes through control of axial chirality by chiral diamines

(matrix presented) The enantio- and diastereomerically pure metal complexes of a chirally dynamic diphenylphosphinoferrocene (DPPF) ligand are obtained through coordination of enantiopure diaminobinaphthyl (DABN) to control the axial chirality of DPPF-Pt,