116159-66-1

Upstream product

• 41527-39-3 dimethyl (2E)-pent-2-enedioate 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 196491-73-3 dimethyl 2-methoxycarbonyl-3-dimethyl(phenyl)silyl-1,5-pentanedioate 
• 88761-82-4 methyl β-(E)-2-dimethylphenylsilylacrylate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 91076-17-4 dimethyl(phenyl)(prop-1-en-2-yl)silane 

Downstream Products

• 223436-83-7 3-(Dimethyl-phenyl-silanyl)-pentanedioic acid 
• 134208-73-4 (S)-3-Hydroxy-4-((S)-1-phenyl-ethylcarbamoyl)-butyric acid 
• 121331-23-5 (3S,1'S)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(1-phenylethyl)amino]-5-oxopentanoic acid, methyl ester 
• 196491-68-6 3-[dimethyl(phenyl)silyl]glutaric anhydride 
• 223437-40-9 (S)-3-Hydroxy-4-((S)-1-phenyl-ethylcarbamoyl)-butyric acid methyl ester 
• 223437-38-5 (S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-hydroxy-5-oxo-pentanoic acid ((S)-1-phenyl-ethyl)-amide 
• 196491-90-4 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid 
• 196491-79-9 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid benzyl ester 
• 223117-71-3 (S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid tert-butyl ester 
• 223118-72-7 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid tert-butyl ester 

Relevant academic research and scientific papers

Stereocontrol in organic synthesis using silicon-containing compounds. Studies directed towards the synthesis of ebelactone A

Several approaches to the synthesis of ebelactone A 2 are described, culminating in the synthesis of the benzenesulfonate of 2-epi-ebelactone A 161. All the approaches were based on three fragments A, B and C, originally defined in general terms in Scheme 1, but eventually used as the aldehyde 72, the allenylsilane 3 and the aldehyde 139, respectively. They were joined, first B with C, and then B+C with A. In the main routes to fragments A and C, the relative stereochemistry was controlled by highly stereoselective enolate methylations 66 → 67, 68 → 69, and 135 → 136, in each case anti to an adjacent silyl group, and by a highly stereoselective hydroboration of an allylsilane 137 → 138, also anti to the silyl group. The hydroxyl groups destined to be on C-3 and C-11 were unmasked by silyl-to-hydroxy conversions 69 → 70 and 138 → 139 with retention of configuration. The stereochemistry created in the coupling of fragment B to C was controlled by the stereospecifically anti SE2′ reaction between the enantiomerically enriched allenylsilane 3 and the aldehyde 139. The double bond geometry was controlled by syn stereospecific silylcupration 148 → 151, and preserved by iododesilylation 151 → 152 of the vinylsilane with retention of configuration, and Nozaki-Hiyama-Kishi coupling with the aldehyde 72 gave the whole carbon skeleton 153 of ebelactone A with the correct relative configuration, all of which had been controlled by organosilicon chemistry. In the steps to remove the superfluous allylic hydroxyl, an intermediate allyllithium species 156 abstracted the proton on C-2, and its reprotonation inverted the configuration at that atom. Other routes to the fragments A and C were also explored, both successful and unsuccessful, both silicon-based and conventional, and a number of unexpected side reactions were investigated.

Catalyst for bisalkoxycarbonylation of olefins, and method for production of succinate derivatives

A catalyst for the bisalkoxycarbonylation of olefins comprising a noble metal compound and a phosphine chalcogenide of the following formula (1): wherein each of R1, R2 and R3 is, independently, an alkyl group or an aryl group each of which may have a substituent, and A is a Group 16 element of the Periodic Table; and R1, R2 or R3 may be combined, directly or through a bridging group, with one another where the groups to be combined may be attached either to an identical phosphorus atom or to different phosphorus atoms. Element A includes oxygen, sulfur and selenium atoms. The noble metal compound includes palladium(II) halides and other palladium compounds. The catalyst may further include a copper(I) halide or other copper compound as a co-catalyst. The use of this catalyst can provide the bisalkoxycarbonylation of olefins with efficiency.

Desymmetrization of prochiral anhydrides with Evans' oxazolidinones: An efficient route to homochiral glutaric and adipic acid derivatives

The prochiral recognition between enantiotopic carbonyl groups in the reaction of 3-substituted glutaric and 3,4-disubstituted adipic anhydrides with anions of Evans' oxazolidinones has been investigated. Each of the σ-symmetric anhydrides provided a diastereoisomeric mixture of half-acids which were separated either by fractional crystallization or by column chromatography of their esters. The diastereoselectivity of the desymmetrization reaction is dependent on the substituents present in the anhydrides.

Phosphine sulfides: Novel effective ligands for the palladium-catalyzed bisalkoxycarbonylation of olefins

Phosphine sulfides were found to be effective as a ligand in the palladium(II)-catalyzed bisalkoxycarbonylation of olefins. Aromatic olefins and vinylsilanes were converted into the corresponding succinates in high yields under mild conditions. Enantiosel