141978-59-8

Upstream product

• 2163-42-0 2-methyl-1.3-propanediol 
• 98-88-4 benzoyl chloride 
• 87092-43-1 1-O,2-O-dibenzoyl-2-methylpropane-1,3-diol 
• 769-78-8 vinyl benzoate 
• 112057-72-4 (RS)-1-benzoyloxy-2-methylpropan-3-ol 
• 141885-93-0 Benzoic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl ester 

Downstream Products

• 914641-65-9 (S)-2-methyl-3-oxopropyl benzoate 
• 141885-92-9 Benzoic acid (S)-3-acetoxy-2-methyl-propyl ester 

Relevant academic research and scientific papers

Synthesis of the C(1)-C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C-C Bond Formation

The C(1)-C(13) fragment of the antimitotic marine macrolide leiodermatolide is prepared in seven steps via hydrogenative and transfer-hydrogenative reductive C-C couplings. A hydrogen-mediated reductive coupling of acetylene with a Roche-type aldehyde is used to construct C(7)-C(13). A 2-propanol-mediated reductive coupling of allyl acetate with (E)-2-methylbut-2-enal at a low loading of iridium (1 mol %) is used to construct C(1)-C(6), which is converted to an allylsilane using Oestereich's copper-catalyzed allylic substitution of Si-Zn reagents. The union of the C(1)-C(6) and C(7)-C(13) fragments is achieved via stereoselective Sakurai allylation.

Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: A powerful entry into chiral building blocks

The asymmetric acylation of meso-2-substituted-1,3-propanediols by using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2-alkyl- and 2-aryl-1,3-propanediols can be desymmetrized in high yields and enantioselectivities by using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized product can be obtained from the same starting material. The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities.

Lipase-catalyzed alcoholysis of diol dibenzoates: Selective enzymatic access to the 2-benzoyl ester of 1,2-propanediol and preparation of the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol

Enzymatic debenzoylation of 1,2-propanediol dibenzoate with 1-octanol has been studied in organic solvent using lipases from different sources. In general a slow, highly regioselective alcoholysis in diisopropyl ether affords exclusively a monoester benzoylated at the secondary hydroxy group although the reaction proceeds with low enantioselectivity. In the presence of Pseudomonas cepacia lipase absorbed onto celite, a faster reaction allows the preparation of the 2-benzoyl ester of (R)-1,2-propanediol (82% ee) and the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol (>98% ee).

Asymmetrization of 2-methylpropane-1,3-diol by Mucor miehei lipase-catalyzed benzoylation in organic solvent

Asymmetrization of prochiral 2-methylpropane-1,3-diol by Mucor miehei lipase (MML)-catalyzed acylation with vinyl benzoate affords the corresponding (S)-monobenzoate (65% ee), that can be obtained enantiomerically pure in 40% yield by a sequential benzoyl

Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst

A dinuclear asymmetric zinc catalyst generated by mixing a 2:1 ratio of diethylzinc and 2,6-bis[5-2-diarylhydroxy methyl-1-pyrrolidinyl]-4-methylphenol has been contrasted with enzymes for the desymmetrization of some meso diols. The best ligand has a p-b

Enantioselective transesterification of 2-methyl-1,3-propanediol derivatives catalyzed by Pseudomonas fluorescens lipase in an organic solvent

The irreversible transesterification of racemic 2-methyl-1,3-propanediol derivatives, the monoethers 3a, 3b, 5a, and the monobenzoate 5b, with vinyl acetate catalyzed by Pseudomonas fluorescens lipase in chloroform affords enantiomerically pure chiral synthons.