1025044-87-4

Upstream product

• 782498-45-7 C₉H₉ClO₂ 
• 89-98-5 2-chloro-benzaldehyde 
• 75-07-0 acetaldehyde 
• 1794-45-2 2-chlorocinnamaldehyde 
• 108-05-4 vinyl acetate 

Downstream Products

• 1025045-04-8 (R)-3-(2-chlorophenyl)-3-hydroxypropyl benzoate 

Relevant academic research and scientific papers

Asymmetric Synthesis of γ-Hydroxy Pinacolboronates through Copper-Catalyzed Enantioselective Hydroboration of α,β-Unsaturated Aldehydes

We report a copper-catalyzed enantioselective hydroboration of α,β-unsaturated aldehydes with pinacolborane. α,β-Unsaturated aldehydes were converted to the corresponding γ-pinacolboronate alcohols in good yields and enantioselectivities through consecutive hydroboration of the C=O and C=C bonds. This process provides simple access to the hydroborated product of allylic alcohols, and the resulting γ-pinacolboronate alcohols could be utilized in various transformations.

Enantioselective Aldol Addition of Acetaldehyde to Aromatic Aldehydes Catalyzed by Proline-Based Carboligases

Aromatic β-hydroxyaldehydes, 1,3-diols, and α,β-unsaturated aldehydes are valuable precursors to biologically active natural products and drug molecules. Herein we report the biocatalytic aldol condensation of acetaldehyde with various aromatic aldehydes to give a number of aromatic α,β-unsaturated aldehydes using a previously engineered variant of 4-oxalocrotonate tautomerase [4-OT(M45T/F50A)] as carboligase. Moreover, an efficient one-pot two-step chemoenzymatic route toward chiral aromatic 1,3-diols has been developed. This one-pot chemoenzymatic strategy successfully combined a highly enantioselective aldol addition step catalyzed by a proline-based carboligase [4-OT(M45T/F50A) or TAUT015] with a chemical reduction step to convert enzymatically prepared aromatic β-hydroxyaldehydes into the corresponding 1,3-diols with high optical purity (e.r. up to >99:1) and in good isolated yield (51-92%). These developed (chemo)enzymatic methodologies offer alternative synthetic choices to prepare a variety of important drug precursors.

Highly enantioselective tandem enzyme-organocatalyst crossed aldol reactions with acetaldehyde in deep-eutectic-solvents

Deep-eutectic-solvents (DES), e.g. choline chloride and glycerol, have emerged as promising bio-based and cost-effective reaction media. Herein, the first concept of tandem catalysis of enzymes and organocatalysts in such environmentally-friendly DES is r

Organocatalytic direct asymmetric crossed-aldol reactions of acetaldehyde in aqueous media

A new type of diarylprolinol-based catalyst, which contains a dioctylamino group in the presence of a newly developed ionic liquid supported (ILS) benzoic acid as cocatalyst, is shown to be an effective catalytic system for the asymmetric direct crossed-aldol reaction of acetaldehyde in aqueous media using brine. For the reactions studied, the catalyst loading could be reduced to 5 mol %; high yields (up to 97%) and high enantioselectivities (up to 92% ee) were also achieved for a wide variety of aromatic aldehyde.

Chiral primary amine catalyzed asymmetric direct cross-aldol reaction of acetaldehyde

The first primary aminocatalytic direct cross-aldol reaction of acetaldehyde is presented. Among the various vicinal diamines screened, the L-tert-leucine derivative 1c in conjunction with (H4SiW 12O40)0.25 was identified as the optimal catalyst; good catalytic activity (up to 99% yield in 4 h), and high enantioselectivities (up to 92% ee) were achieved for a range of donors, including aromatic aldehydes and isatin derivatives. Aqueous acetaldehyde solution and paraldehyde can be conveniently applied in this system.

Tandem catalysis by lipase in a vinyl acetate-mediated cross-aldol reaction

The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate-mediated aldol reaction. The reaction was facilitated through the lipase-catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal side product formation.

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