133271-00-8

Upstream product

• 100-52-7 benzaldehyde 
• 85551-57-1 (R)-1-Phenylbut-3-en-1-ol 
• 181227-42-9 (+)-(R)-1-phenylbut-3-en-1-yl acetate 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 1452591-09-1 (R,E)-3-(4-hydroxy-4-phenylbut-1-en-1-yl)cyclohex-2-en-1-one 
• 75-07-0 acetaldehyde 

Downstream Products

• 2768-42-5 (R)-3-phenyl-3-hydroxypropionic acid 
• 5381-93-1 (4R)-4-hydroxy-4-phenylbutan-2-one 
• 115290-81-8 (R)-N-methyl-3-phenyl-3-hydroxypropylamine 
• 103548-16-9 (R)-3-phenyl-1,3-dihydroxypropane 

Relevant academic research and scientific papers

Highly efficient enzymatic resolution of homoallyl alcohols leading to a simple synthesis of optically pure fluoxetine and related compounds

A practical method for enzymatic resolution of homoallyl alcohols and its utility in the synthesis of optically pure fluoxetine and related compounds is reported.

Proline-based polymeric monoliths: synthesis, characterization, and applications as organocatalysts in aldol reaction

Proline-based polymer monoliths were synthesized via green protocol using lipase-catalyzed esterlfication of methacrylic acid and 4-hydroxyproline. Prolinyl methacrylate thus prepared was polymerized in situ as crosslinked monolith. The monolith was chara

A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs

Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde into η6-benzaldehyde Cr(CO)3 circumvents this limitation. Asymmetric synthesis of (R)-Phenoperidine, as well as formal syntheses of (R)-Fluoxetine and (R)-Atomoxetine, illustrate the benefits of this strategy.

Heterogeneous versus homogeneous copper(II) catalysis in enantioselective conjugate-addition reactions of boron in water

We have developed CuII-catalyzed enantioselective conjugate-addition reactions of boron to α,β-unsaturated carbonyl compounds and α,β,γ,δ-unsaturated carbonyl compounds in water. In contrast to the previously reported CuI catalysis that required organic solvents, chiral CuII catalysis was found to proceed efficiently in water. Three catalyst systems have been exploited: cat. 1: Cu(OH)2 with chiral ligand L1; cat. 2: Cu(OH)2 and acetic acid with ligand L1; and cat. 3: Cu(OAc)2 with ligand L1. Whereas cat. 1 is a heterogeneous system, cat. 2 and cat. 3 are homogeneous systems. We tested 27 α,β-unsaturated carbonyl compounds and an α,β-unsaturated nitrile compound, including acyclic and cyclic α,β-unsaturated ketones, acyclic and cyclic β,β- disubstituted enones, acyclic and cyclic α,β-unsaturated esters (including their β,β-disubstituted forms), and acyclic α,β-unsaturated amides (including their β,β-disubstituted forms). We found that cat. 2 and cat. 3 showed high yields and enantioselectivities for almost all substrates. Notably, no catalysts that can tolerate all of these substrates with high yields and high enantioselectivities have been reported for the conjugate addition of boron. Heterogeneous cat. 1 also gave high yields and enantioselectivities with some substrates and also gave the highest TOF (43 200 h-1) for an asymmetric conjugate-addition reaction of boron. In addition, the catalyst systems were also applicable to the conjugate addition of boron to α,β,γ, δ-unsaturated carbonyl compounds, although such reactions have previously been very limited in the literature, even in organic solvents. 1,4-Addition products were obtained in high yields and enantioselectivities in the reactions of acyclic α,β,γ,δ-unsaturated carbonyl compounds with diboron 2 by using cat. 1, cat. 2, or cat. 3. On the other hand, in the reactions of cyclic α,β,γ,δ-unsaturated carbonyl compounds with compound 2, whereas 1,4-addition products were exclusively obtained by using cat. 2 or cat. 3, 1,6-addition products were exclusively produced by using cat. 1. Similar unique reactivities and selectivities were also shown in the reactions of cyclic trienones. Finally, the reaction mechanisms of these unique conjugate-addition reactions in water were investigated and we propose stereochemical models that are supported by X-ray crystallography and MS (ESI) analysis. Although the role of water has not been completely revealed, water is expected to be effective in the activation of a borylcopper(II) intermediate and a protonation event subsequent to the nucleophilic addition step, thereby leading to overwhelmingly high catalytic turnover. Copyright

A diarylprolinol in an asymmetric, catalytic, and direct crossed-aldol reaction of acetaldehyde

(Chemical Equation Presented) No over-reacting: A diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of acetaldehyde, affording β-hydroxy α-unsubstituted aldehydes in good yield with excellent enantio

C-C ASYMMETRIC BOND FORMATION MEDIATED BY OPTICALLY ACTIVE SULFOXIDES

Highly stereoselective C-C bond forming reactions can be performed with a variety of optically active sulfinyl derivatives to afford, after desulfurization, optically active sulfur-free products.