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Upstream product

• 3393-45-1 5,6-dihydro-pyran-2-one 
• 5720-07-0 4-methoxyphenylboronic acid 
• 28252-86-0 3-(4-methoxyphenyl)pentane-1,5-diol 
• 189884-50-2 (+)-2-[1-(4-methoxy-phenyl)-allyl]-malonic acid dimethyl ester 
• 57171-24-1 3-(4-methoxyphenyl)glutaric anhydride 
• 865367-05-1 (S)-3-(4-methoxyphenyl)-glutaric acid monobenzyl ester 
• 865367-06-2 (S)-3-(4-methoxyphenyl)-glutaric acid monoallyl ester 
• 865367-03-9 (S)-3-(4-methoxyphenyl)-glutaric acid monomethyl ester 
• 860012-02-8 (S)-3-(4-methoxyphenyl)-glutaric acid monoethyl ester 
• 33868-91-6 3-(4-methoxyphenyl)glutaric acid 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Regio- and enantio-selective allylic alkylation catalysed by a chiral monophosphine-palladium complex

Allylic alkylation of racemic 1-arylprop-2-enyl acetates [ArCH(OAc)CH=CH2] with the sodium enolate of dimethyl methylmalonate in the presence of a palladium catalyst coordinated with (R)-2-diphenylphosphino-2′-methoxy-1,1′-binaphthyl [(R)-MeO-MOP] proceeds with high branch selectivity (90%) to give chiral products [ArC*H-(Nu)CH=CH2] of up to 87% ee.

A New Type of Chiral Cyclic Sulfinamide–Olefin Ligands for Rhodium-Catalyzed Asymmetric Addition

A new type of chiral cyclic sulfinamide–olefin ligands, N-allylic 2,3-dihydro-1,2-benzoisothiazole 1-oxides, with 2,3-dihydro-1,2-benzoisothiazole 1-oxide as a unique chiral skeleton, is developed for the highly enantioselective rhodium-catalyzed asymmetr

Enantioselective preparation of δ-valerolactones with horse liver alcohol dehydrogenase

Horse liver alcohol dehydrogenase (HLADH) has been found to be a versatile biocatalyst for the desymmetrization of prochiral 3-arylpentane-1,5-diols, based on a two-step one-pot oxidation. This procedure has allowed the formation of valuable (S)-lactones in good to excellent conversions and enantiomeric excess. The catalytic performance of HLADH has been studied using several cofactor regeneration systems and cosolvents, finding great improvements in terms of activity with L-lactate dehydrogenase, while the stereoselectivity of the process was significantly improved when using tetrahydrofuran. Docking studies has revealed the pattern substitution importance in the selectivity and activity of this oxidative process. Not just horsing around: Horse liver alcohol dehydrogenase is found to be a versatile biocatalyst for the desymmetrization of 3-arylpentane-1,5-diols through a two-step one-pot oxidation. The catalytic performance of horse liver alcohol dehydrogenase (HLADH) is studied with several cofactor regeneration systems and cosolvents. Docking studies reveal the importance of pattern substitution in the selectivity and activity of this biotransformation.

Rh-IndOlefOx catalyzed conjugate addition/Heck-type coupling of organoboronics to a lactam or a lactone

Four indole-olefin-oxazoline (IndOlefOx) ligands were synthesized and evaluated in Rh-catalyzed reactions between organoboronics and a lactam or a lactone. In addition to the expected conjugate addition products, the formation of significant amounts of Heck-type products was observed. The scope and limitations of these reactions were investigated.

Highly active rhodium catalyst with electron-poor diphosphine enables efficient synthesis of chiral 4-aryl-δ-lactones

Chiral 4-aryl-δ-lactones could be synthesized efficiently with high enantioselectivity through asymmetric 1,4-addition of arylboronic acid to α,β-unsaturated lactones using Rh catalyst including electron-poor diphosphine (MeO-F12-BIPHEP) at room temperature for 1 h. In particular, our catalytic system proved to be applicable to relatively large coumarin analogues, giving optically pure 4-phenylchroman-2-one analogues in a short time.

Enzymatic desymmetrization of 3-arylglutaric acid anhydrides

Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4.

Asymmetric Michael Additions via SAMP-/RAMP-Hydrazones Enantioselective Synthesis of β-Substituted δ-Oxopentanoates and δ-Lactones

Asymmetric Michael addition of metalated acetaldehyde SAMP- or RAMP-hydrazone (S)- or (R)-2 to α,β-unsaturated esters 3 and subsequent oxidative cleavage by ozonolysis yields the β-substituted δ-oxopentanoates (R)- or (S)-5 with high enantiomeric excesses (ee = 90 to >/= 96percent).Racemization-free reduction and cyclization affords the corresponding optically active δ-lactones (R)- or (S)-7.