59357-09-4

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 78-84-2 isobutyraldehyde 
• 202744-37-4 trichloro<<1-(methylethyl)ethenyl>oxy>silane 
• 17510-45-1 2-(trimethylsilyloxy)-3-methyl-1-butene 

Downstream Products

• 103668-49-1 (1S*,3R*)-4-Methyl-1-phenylpentane-1,3-diol 
• 103668-44-6 (1SR,1RS)-1-phenyl-4-methylpentane-1,3-diol 

Relevant academic research and scientific papers

SmI(2)-promoted oxidation of aldehydes in the presence of electron-rich heteroatoms.

[reaction: see text] The Evans-Tishchenko reaction provides an efficient and practical solution for the oxidation of aldehydes possessing sensitive electron-rich heteroatoms to the corresponding esters. Careful selection of the sacrificial beta-hydroxy ke

Vanadyl species-catalyzed complementary β-oxidative carbonylation of styrene derivatives with aldehydes

A series of oxometallic species and metal acetylacetonates (acac) was examined as catalysts for oxidative carbonylation of styrene with benzaldehyde using t-butylhydroperoxide as the co-oxidant in warm acetonitrile. Among them, VO((acac)2 and vanadyl(iv) chloride were found to be the only catalyst class to achieve cross-coupling processes by judiciously tuning the ligand electronic attributes, leading to β-hydroxylation- and β-peroxidation-carbonylation of styrene, respectively, in a complementary manner. Mechanistic studies indicated that vanadyl-associated acyl radicals generated by t-butoxy radical-assisted, homolytic cleavage of the aldehyde C-H bond were involved in tandem processes with an exclusive syn diastereoselectivity in the case of β-methylstyrene. This journal is

Mixed alkylamido aluminate as a kinetically controlled base

The mechanisms by which directed ortho metalation (DoM) and postmetalation processes occur when aromatic compounds are treated with mixed alkylamido aluminate i-Bu3Al(TMP)Li (TMP-aluminate 1; TMP = 2,2,6,6- tetramethylpiperidide) have been inve

Directed reductive amination of β-hydroxy-ketones: Convergent assembly of the ritonavir/lopinavir core

(Chemical Equation Presented) An efficient procedure for the directed reductive amination of β-hydroxy-ketones (3) for the stereoselective preparation of 1,3-syn-amino alcohols (6) is reported. The operationally simple protocol uses Ti(iOPr)su

Anti-selective and regioselective aldol addition of ketones with aldehydes using MgI2 as promoter

The first example of a direct aldehyde-ketone coupling using the secondary amine piperidine as base in the presence of MgI2 to generate high selectivity of anti-aldol products from unmodified ethyl ketones in high yield is reported. The couplin

The chemistry of trichlorosilyl enolates. Aldol addition reactions of methyl ketones

Investigations on the aldol addition chemistry of trichlorosilyl enolates derived from methyl ketones are presented in full. These trichlorosilyl enolates are competent aldol reagents in the absence of additives, reacting with aldehydes at ambient temperature to provide high yields of aldol adducts. When either enol or aldehyde partner bears a stereogenic center, low diastereoselectivity is observed in this uncatalyzed aldol process. The aldol additions are dramatically accelerated by the addition of catalytic quantities of chiral phosphoramides, particularly one derived from N,N'-dimethylstilbene-1,2-diamine. In this catalyzed mode, good to high enantioselectivities are obtained with a variety of achiral trichlorosilyl enolates and aldehydes. When either partner bears a stereogenic center, high diastereoselectivities are obtained with one enantiomer of the catalyst (matched case), while the other enantiomer provides low diastereoselectivity (mismatched case). The reaction scope, optimization of conditions, and stereoselection events are also discussed.

Bis(amido)magnesium mediated aldol additions: First structural characterisation of an amidomagnesium aldolate intermediate

Bis(hexamethyldisilazido)magnesium has successfully been used to mediate aldol additions of selected ketones and aldehydes in hydrocarbon media, and the structure of an intermediate amido(aldolate), [{(Me3Si)2NMg[μ-OC(Me)-Bu(t)CHsub

Cobalt(II) catalysed reaction of alkenes with aliphatic aldehydes and molecular oxygen: Scope and mechanism

A variety of cobalt(II) complexes can be prepared using Schiff's bases derived from aromatic aldehydes and amines or α-aminoesters. These complexes are versatile catalyst for the reaction between aliphatic aldehydes and various alkenes. The outcome of the reaction is controlled by the electronic nature of the alkene as the electron deficient alkenes undergo oxidative addition of aldehydes followed by dioxygen incorporation to yield 2-hydroxy(acyloxy)-4-oxoesters or nitriles whereas unactivated or electron rich alkenes afford the corresponding epoxides. These reactions are proceeding via a radical pathway and a common acylcobalt intermediate is proposed for the formation of 4 as well as the epoxides 7.

STUDIES ON THE DIASTEREOSELECTIVE REDUCTION OF β-HYDROXY KETONES TO 1,3-DIOLS WITH COMMON HYDRIDE REAGENTS

Some common reducing agents were employed in the diastereoselective reduction of several β-hydroxy ketones to their corresponding syn-1,3-diols.The use of NaBH4 with a Ti(IV) chelating species produced syn diols with a moderate to good selectivity significantly depending upon the reaction conditions chosen (solvent, temperature, nature of the titanium species).The use of LiAlH4 at low temperature, in the presence of LiI, showed a high selectivity for reduction to syn diols, thus demonstrating a possible chelating role of lithium.Some interesting preliminary results have been also obtained in the diastereoselective reduction of MEM-protected β-alkoxy ketones.