166191-24-8

Upstream product

• 5411-56-3 (1S)-1-(2-bromophenyl)ethanol 
• 77-78-1 dimethyl sulfate 
• 2142-69-0 2-bromophenyl methyl ketone 
• 74-88-4 methyl iodide 

Downstream Products

• 215316-66-8 (S)-1-iodo-2-(1-methoxyethyl)benzene 
• 166191-23-7 (-)-(S)-2-(1-methoxyethyl)benzeneboronic acid 
• 215317-06-9 (S)-bis(acetato-O)[2-(1-methoxyethyl)phenyl]iodine 
• 170379-94-9 1,2-bis(2-((S)-1-methoxyethyl)phenyl)diselane 

Relevant academic research and scientific papers

Enantiopurity and absolute configuration determination of arene cis-dihydrodiol metabolites and derivatives using chiral boronic acids

The relative merits of the methods employed to determine enantiomeric excess (ee) values and absolute configurations of chiral arene and alkene cis-1,2-diol metabolites, including boronate formation, using racemic or enantiopure (+) and (?)-2-(1-methoxyet

New chiral hypervalent iodine compounds in asymmetric synthesis

The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrène and in the a-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

The Mechanism of Double Olefination Using Titanium-Substituted Ylides

The adduct 3, derived from TiCl3(OiPr) and (Me2N)3P=CH2, engages in a complicated set of interactions with NaN(SiMe3)2 and aldehydes, resulting in the requirement to use excess amounts of both reagents for the one-pot synthesis of allenes. When TiCl2(OiPr)2 is used instead, ligand substitution reactions with NaN(SiMe3)2 are diminished and so stepwise transformations can be accomplished without excess amounts of each reagent. The selective production of vinylphosphonium salts and byproduct titanium oxides from Ti-substituted ylides and aldehydes is proposed to arise from the presence of a chloride leaving group on the metal. Isolated vinylphosphonium compounds may be deprotonated with phenyllithium to give thermally sensitive allenic phosphoranes, which have been characterized by low temperature multinuclear NMR. The reaction of allenic phosphoranes with aldehydes affords oxaphosphetane and betaine intermediates which appear to interconvert upon warming to produce allene and phosphine oxide. Dimethylamino-substituted phosphorus components are required for high yields in both steps of the allene-forming process, presumably to boost the reactivity of the hindered Ti-substituted ylide reagents and to stabilize the allenic phosphorane unit so that it may be trapped by aldehyde. The placement of chiral groups on the phosphorus methylide or aldehyde components results in low levels of enantiomeric and diastereomeric induction, respectively, during allene formation. In two cases, the diastereomeric ratios of initially-formed oxaphosphetanes have been found to differ from the diastereomeric composition of their product allenes, offering examples of the phenomenon known as "stereochemical drift". However, oxaphosphetane/betaine formation from allenic phosphorane and aldehyde has been found to be irreversible, suggesting that an intramolecular betaine olefin isomerization is responsible for the loss of stereochemical integrity during the Wittig step.

Phosphane ligands with two binding sites of differing hardness for enantioselective Grignard cross coupling

A series of new, chiral phosphanes is presented, individual members of which were designed to serve as ligands in transition-metal mediated asymmetric Grignard cross coupling reactions. These ligands are characterized by a side chain containing one or two oxygen atoms with the capacity to act as binding sites for the incoming Grignard reagent. A number of structural parameters for the compounds was varied to learn about the reaction mechanism. Most of the ligands were tested in two cross coupling reactions, the formation of 3-phenylbut-1-ene and of 2,2′-dimethyl-1,1′-binaphthyl, respectively. Although both systems gave modest enantiomeric excesses it was not possible to make a comparison of their respective abilities.

Asymmetrische Umsetzung von Arylalkenen mit Diseleniden

Stichworte: Arylalkene; Asymmetrische Synthesen; Chirale Diselenide; Selenverbindungen