206446-98-2

Upstream product

• 122-78-1 phenylacetaldehyde 
• 67-64-1 acetone 
• 1118-84-9 allyl acetoacetate 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 100303-82-0 1-methoxy-2-phenylethanol 
• 61077-65-4 1-phenylpent-4-en-2-ol 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 3318-61-4 1-phenyl-2,4-pentanedione 

Relevant academic research and scientific papers

Selective access to all four diastereomers of a 1,3-amino alcohol by combination of a keto reductase- and an amine transaminase-catalysed reaction

The biocatalytic synthesis of chiral amines has become a valuable addition to the chemists' toolbox. However, the efficient asymmetric synthesis of functionalised amines bearing more than one stereocentre, such as 1,3-amino alcohols, remains challenging. By employing a keto reductase (KRED) and two enantiocomplementary amine transaminases (ATA), we developed a biocatalytic route towards all four diastereomers of 4-amino-1-phenylpentane-2-ol as a representative molecule bearing the 1,3-amino alcohol functionality. Starting from a racemic hydroxy ketone, a kinetic resolution using an (S)-selective KRED provided optically active hydroxy ketone (86% ee) and the corresponding diketone. Further transamination of the hydroxy ketone was performed by either an (R)- or an (S)-selective ATA, yielding the (2R,4R)- and (2R,4S)-1,3-amino alcohol diastereomers. The remaining two diastereomers were accessible in two subsequent asymmetric steps: the diketone was reduced regio- and enantioselectively by the same KRED, which yielded the (S)-configured hydroxy ketone. Eventually, the subsequent transamination of the crude product with (R)- and (S)-selective ATAs yielded the remaining (2S,4R)- and (2S,4S)-diastereomers, respectively.

One-pot reduction-aldol reaction of esters

We have developed a new protocol for making aldol adducts in a one-pot reaction between esters and silyl enol ethers in the presence of DIBALH without isolating the intermediate aldehydes. Lewis acid activation of the initially formed aluminated hemiacetals produces highly reactive electrophilic aldehyde equivalents in situ. Using this protocol, various aldol adducts can be readily obtained in up to 90% yield on a large scale.

Decarboxylative aldol reactions of allyl β-keto Esters via heterobimetallic catalysis

Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl β-keto esters have been developed. The reaction is promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl β-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis in which the optimized reaction conditions require the addition of both metals. Copyright

Directed methallylations as a synthetic route to 1,3-polyols

The directed methallylation of β-hydroxyaldehydes and ketones with methallylboronic acid is examined. The reaction proceeds with good to excellent selectivity with ketones.