99192-57-1

Upstream product

• 100-52-7 benzaldehyde 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 71699-15-5 (1R*,2R*)-1-hydroxy-2-methyl-1-phenyl-3-pentanone 
• 96-22-0 pentan-3-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 95736-14-4 tert-butyldimethyl silyl enol ether of 3-pentanone 

Relevant academic research and scientific papers

Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions

The marine natural product (+)-discodermolide was first isolated in 1990 and, to this day, remains a compelling synthesis target. Not only does the compound possess fascinating biological activity, but it also presents an opportunity to test current methods for chemical synthesis and provides an inspiration for new reaction development. A new synthesis of discodermolide employs a previously undisclosed stereoselective catalytic diene hydroboration and also establishes a strategy for the alkylation of chiral enolates. Furthermore, this synthesis of discodermolide provides the first examples of the asymmetric 1,4-diboration of dienes and borylative diene-aldehyde couplings in complex-molecule synthesis. Borylation-based synthesis: The development of a strategy for stereocontrol in catalytic diene hydroboration enables the synthesis of a critical building block for the assembly of (+)-discodermolide. Combined with asymmetric catalytic diboration, hydroformylation, and borylative aldehyde-diene coupling reactions, (+)-discodermolide could then be prepared from simple hydrocarbon-based building blocks.

Synthesis of cyclobutanones and four-membered enol ethers by using a rearrangement reaction of enol triflates

A new synthetic method of cyclobutanone derivatives and four-membered enol ethers via an intramolecular cyclization of a ketone enolate was developed. The cyclization precursors, enol triflates having a silyloxy group at the β′-position, were synthesized from the corresponding β-hydroxy ketones, which were prepared via an aldol reaction of a cycloalkanone and an aldehyde. Under the influence of TBAF, the enol triflates afforded a cyclobutanone or a four-membered enol ether through rearrangement of the trifluoromethanesulfonyl group followed by an intramolecular C- or O-alkylation reaction.

New role of tin(II) compounds in organic synthesis

Three new carbon-carbon bond forming reactions by the use of new catalyst systems involving tin(II) compounds are described in this article.The aldol reaction of silyl enol ethers with acetals or aldehydes and the Michael reaction of silyl enol ethers wit

An Efficient and Extremly Mild Catalyst System, Combined Use of Trityl Chloride and Tin(II) Chloride, in the Aldol and Michael Reactions

The aldol reaction of silyl enol ethers with acetals or aldehydes, and the Michael reaction of silyl enol ethrs with α,β-unsaturated ketones are efficiently catalyzed by the combined use of trityl chloride and tin(II) chloride under extremly mild conditio

TRITYL SALTS AS EFFICIENT CATALYSTS IN THE ALDOL REACTION

In the presence of a catalytic amount of trityl salts, such as TrOTf, TrSbCl6, TrPF6, TrSnCl5, etc., silyl enol ethers react with aldehydes to give the corresponding aldols in good yields.The preferential formations of erythro or threo aldols become possi

AN EFFICIENT METHOD FOR THE PREPARATION OF THREO CROSS-ALDOLS FROM SILYL ENOL ETHERS AND ALDEHYDES USING TRITYL PERCHLORATE AS A CATALYST

Threo cross-aldol products are predominantly formed in good yields by treating tert-butyldimethylsilyl enol ethers with aldehydes in the presence of a catalytic amount of trityl perchlorate.