17226-81-2

Upstream product

• 100-52-7 benzaldehyde 
• 140-88-5 ethyl acrylate 
• 105-37-3 Ethyl propionate 
• 37442-45-8 ethyl 2-(hydroxy(phenyl)methyl)propenoate 
• 10488-87-6 ethyl 2-benzoylpropionate 
• 80675-53-2 1-ethoxy-1-trimethylsiloxyprop-1-ene 
• 207446-11-5 2-dimethylsilanyl-propionic acid ethyl ester 
• 7042-33-3 ethyl 2-methylcinnamate 
• 80523-18-8 ((2S,3S)-2-Methyl-3-phenyl-oxiranyl)-methanol 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 64-17-5 ethanol 
• 76638-09-0 trans-2-methyl-3-phenyloxirane-2-carbaldehyde 
• 153645-09-1 ethyl 2-bromo-3-hydroxy-2-methyl-3-phenylpropanoate 
• 535-11-5 Ethyl 2-bromopropionate 

Downstream Products

• 128887-13-8 3-(2-Fluoro-2-phenyl-acetoxy)-2-methyl-3-phenyl-propionic acid ethyl ester 
• 128887-13-8 3-(2-Fluoro-2-phenyl-acetoxy)-2-methyl-3-phenyl-propionic acid ethyl ester 
• 84784-81-6 erythro-2-methyl-3-phenyl-1,3-propanediol 1-methoxyethoxymethyl ether 
• 57051-07-7 erythro-3-methoxy-2-methyl-1-phenyl-1-propanol 
• 84784-79-2 2-((1R,2S)-3-Methoxy-2-methyl-1-phenyl-propoxy)-tetrahydro-pyran 
• 84784-78-1 (2S,3R)-2-Methyl-3-phenyl-3-(tetrahydro-pyran-2-yloxy)-propan-1-ol 
• 62509-81-3 3-methoxy-2-methyl-1-phenylpropan-1-one 
• 14366-91-7 syn-2-methyl-1-phenyl-1,3-propanediol 
• 84784-77-0 (2R,3R)-2-Methyl-3-phenyl-3-(tetrahydro-pyran-2-yloxy)-propionic acid ethyl ester 
• 7087-77-6 (1S,2S)-2-methyl-1-phenyl-propane-1,3-diol 

Relevant academic research and scientific papers

Synthesis and Applications of Unquaternized C-Bound Boron Enolates

A general and facile method to prepare unquaternized C-bound boron enolates by a ligand-controlled O-to-C isomerization is reported. Using this protocol, C-bound pinacolboron enolates have been isolated in pure form for the first time, and have been fully characterized by NMR spectroscopy and X-ray crystallography. In contrast to the general perception, such C-boron enolates are stable without coordinative saturation at the boron. Moreover, C-boron enolates present reactivities that are distinct from the O-boron enolates, and their applications in C-O and C-C bond formations are demonstrated.

Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases

α-Alkyl-β-hydroxy esters were obtained via dynamic kinetic resolution (DKR) employing purified or crude E. coli overexpressed alcohol dehydrogenases (ADHs). ADH-A from R. ruber, CPADH from C. parapsilosis and TesADH from T. ethanolicus afforded syn-(2R,3S) derivatives with very high selectivities for sterically not impeded ketones ('small-bulky' substrates), while ADHs from S. yanoikuyae (SyADH) and Ralstonia sp. (RasADH) could also accept bulkier keto esters ('bulky-bulky' substrates). SyADH also provided preferentially syn-(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti-(2S,3S) derivatives. With anti-Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn-(2S,3R) alcohols were obtained with high conversions and diastereomeric excess in some cases, especially with LBADH. Furthermore, due to the thermodynamically favoured reduction of these substrates, it was possible to employ just a minimal excess of 2-propanol to obtain the final products with quantitative conversions. Copyright

An efficient cobalt(I)-catalysed reformatsky reaction using α-chloro esters

An efficient cobalt(I)-catalysed Reformatsky reaction using α-chloro esters has been developed. The catalyst is prepared by reducing the cobalt(II) chloride (5%)/1,2-bis(diphenylphosphino)ethane (dppe)(5%)/zinc iodide (10%) system with zinc metal in acetonitrile in the presence of both the α-chloro ester and the carbonyl compound; good to excellent conversions to β-hydroxy esters are obtained at room temperature in 2.5 h.

Solvent-free synthesis of β-hydroxy esters and β-amino esters by indium-mediated reformatsky reaction

In a convenient and efficient procedure for the solvent-free synthesis of β-hydroxy esters and β-amino esters, various aldehydes and aldimines undergo a Reformatsky reaction mediated by non-activated indium at room temperature to give the corresponding esters in good to excellent yields. Georg Thieme Verlag Stuttgart.

Catalytic generation of activated carboxylates: Direct, stereoselective synthesis β-hydroxyesters from epoxyaldehydes

The catalytic generation of activated carboxylates from epoxyaldehydes enables the direct, stereoselective synthesis of β-hydroxyesters under mild, convenient reaction conditions. In addition to providing a new method for the synthesis of anti-aldol adducts, this chemistry unveils a mechanistically viable solution to the catalytic, waste-free synthesis of esters. Copyright

Magnesium Bromide Mediated Highly Diastereoselective Heterogeneous Hydrogenation of Olefins

(Matrix Presented) Palladium on carbon combined with magnesium bromide catalyzed hydrogenation of Baylis-Hillman olefins to afford the corresponding aldol derivatives in a highly syn-diastereoselective manner is described.

Enantio- and diastereoselective reductive aldol reactions with iridium-pybox catalysts

(formula presented) A catalytic amount of [(cod)IrCl]2 and indane-pybox converts diethylmethylsilane, methyl acrylate, and certain aldehydes to the derived reductive aldol adduct with good enantio- and diastereocontrol.

A facile preparation of indium enolates and their Reformatsky-and Darzens-type reactions

Indium enolates were readily prepared by transmetalation of lithium enolates with indium trichloride, and were subsequently reacted with aldehydes to give β-hydroxy esters in high yields. Indium α-bromo enolates were also prepared and reacted with carbonyl compounds to give Darzens-type α,β-epoxy carbonyl products. The Royal Society of Chemistry 2000.

Reversed stereochemical control in the presence of CeCl3 and TiCl4 in the Lewis acid mediated reduction of α-alkyl-β-keto esters by metal hydrides. A general methodology for the diastereoselective synthesis of syn- and anti-α-alkyl-β

The Lewis acid-mediated reduction of α-alkyl-β-keto esters has been shown to proceed by different stereochemical control depending on the nature of the metal atom. Strongly chelating TiCl4 led to the syn isomer in high diastereomeric excess in

Uncatalyzed aldol reaction using a dimethylsilyl enolate and α- dimethylsilyl ester in N,N-dimethylformamide

Dimethylsilyl enolates and α-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction.