145624-53-9

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 24506-17-0 3-hydroxy-3-phenylpropionamide 
• 100-52-7 benzaldehyde 
• 202744-35-2 trichloro<(1-butylethenyl)oxy>silane 
• 60585-82-2 2-trimethylsilyloxy-1-hexene 
• 591-78-6 n-hexan-2-one 
• 693-02-7 hex-1-yne 
• 73922-80-2 1-phenylhept-2-yn-1-ol 
• 3017-66-1 2-bromohex-1-ene 

Relevant academic research and scientific papers

Lewis base activation of lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes

(Matrix presented) A highly enantioselective addition of silyl enol ethers derived from simple methyl ketones is described. The catalyst system of silicon tetrachloride activated by a chiral bisphosphoramide (R,R)-7 effectively promotes the addition of a variety of unsubstituted silyl enol ethers to aromatic, olefinic, and heteroaromatic aldehydes in excellent yield.

Gold-Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Catalytic Reaction Pathways to Access 1,3-Amino Alcohols, 3-Hydroxyketones, or 3-Aminoketones

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. First, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxyimines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-amino alcohols with high syn selectivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway. The utility of the new chemistry was exemplified by the one-pot synthesis of a selection of N-arylpyrrolidines and N-arylpiperidines. A mechanism for the hydroamination has been proposed on the basis of experimental studies and density functional theory calculations.

Reductive ring cleavage of nonconjugated Δ2-isoxazolines to β-hydroxy ketones with aluminum and copper(II) chloride

A facile, economic, and efficient protocol for the reduction of nonconjugated Δ2-isoxazolines to the corresponding β-hydroxy ketones using Al/CuCl2 as the reducing agent has been developed. The method is both rapid and complete requiring less than ten minutes to attain total ring cleavage. This is the first example of using an in situ prepared Al/Cu couple in organic synthesis. Georg Thieme Verlag Stuttgart · New York.

Chiral phosphoramide-catalyzed aldol additions of ketone trichlorosilyl enolates. Mechanistic aspects

The mechanism of the catalytic, enantioselective addition of trichlorosilyl enolates to aldehydes has been investigated. Kinetic studies using ReactIR and rapid injection NMR (RINMR) spectroscopy have confirmed the simultaneous operation of dual mechanist

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

Catalytic Asymmetric Aldol-Type Reactions Using a Chiral (Acyloxy)borane Complex

In the presence of 20 molpercent of a chiral (acyloxy)borane (CAB) complex prepared from BH3*THF and a chiral mono-O-acylated tartaric acid, achiral silyl enol ethers or ketene silyl acetals react with achiral aldehydes to afford the corresponding aldol-t

Enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions catalyzed by a tryptophan-derived oxazaborolidine

The (S)-tryptophan derived catalyst 1, has been used to effect enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions of trimethylsilyloxy olefins and dienes.