52117-33-6

Upstream product

• 108-22-5 Isopropenyl acetate 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 67-56-1 methanol 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 22039-97-0 4-methoxy-4-phenyl-1-butene 
• 100-52-7 benzaldehyde 
• 6651-38-3 methyltris[(1-methylvinyl)oxy]silane 
• 35364-99-9 α-chlorobenzyl methyl ether 
• 67-64-1 acetone 
• 201230-82-2 carbon monoxide 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 149-73-5 trimethyl orthoformate 
• 104974-60-9 rac-(Z)-4-phenylbut-3-en-2-ol 
• 51835-45-1 α-methoxybenzyl acetate 

Relevant academic research and scientific papers

The first directed reduction of beta-alkoxy ketones to anti-1,3-diol monoethers: identification of spectator and director alkoxy groups.

A new reduction procedure for the stereoselective reduction of certain beta-alkoxy ketones is described. The method relies upon electron-transfer reduction using samarium diiodide in THF with MeOH as an additive. Reduction is facile for a number of alkoxy

Trisubstituted Highly Activated Benzo[ d]thiazol-2-yl-sulfone-Containing Olefins as Building Blocks in Organic Synthesis

In this paper, we report the formation of highly electrophilic 1,1-deactivated olefins, their use as novel synthetic building blocks, and their transformation to structurally diverse molecular scaffolds. Synthesis of 1,1-deactivated olefins substituted with a BT-sulfonyl group and a carbonyl or nitrile, respectively, consists of unusual Ti(OPri)4-mediated Knoevenagel-type condensation and proceed in good to excellent yields. Generated olefins can be further transformed in a highly stereoselective manner and in good yields to various polyfunctionalized heterocycles and acyclic molecular scaffolds. Overall, the obtained structures are accessed in two to four steps starting from the (mostly) commercially available aldehydes. In addition, the presence of the BT-sulfonyl group in prepared structures allows for further chemoselective functionalization/post-synthetic transformations to provide structurally diverse final compounds.

Acid catalyzed rearrangement of vinyl and ketene acetals

Substituted vinyl and ketene acetals undergo smooth oxygen-to-carbon rearrangement with a catalytic amount of TMSOTf to afford chain-extended ketones or esters, respectively. The developed procedure has been applied to the stereoselective synthesis of C-glycosides from the corresponding anomeric vinyl ethers.

Palladium(II)-catalyzed dicarboxymethylation of chiral allylic alcohols: Chirality transfer affording optically active diesters containing three contiguous chiral centers

This manuscript describes the extension of Stille's palladium-catalyzed olefin dicarbonylation reaction to chiral allylic alcohols with chirality transfer to afford the corresponding chiral alcohol functionalized with bis-carbomethoxy esters, containing three contiguous chiral centers, in good to excellent diastereoselectivities (78-98%).

Iridium-catalyzed crossed aldol coupling and a new concept to form an Ir-Si species

[Ir(COD)(PPh3)2]X (X=PF6, ClO4, and OTf) activated by H2 molecule catalyzes Mukaiyama-type aldol coupling between enoxysilanes and acetals or aldehydes. An Ir-Si species formed in the first stage of t

Electrochemical Wacker Type Reaction with a Double Mediatory System Consisting of Palladium Complex and Tri(4-bromophenyl)amine

The electrochemical Wacker type oxidation of terminal olefins by using palladium chloride or palladium acetate and tri(4-bromophenyl)amine as a recyclable mediator in either a divided cell or an undivided cell afforded the corresponding methyl ketones in good yields.

Aldol-Type Reaction by Propen-2-yl Acetate with NCS/SnCl2/ROH

The addition of N-chlorosuccinimide (NCS) to a solution of propen-2-yl acetate, aldehydes, SnCl2, and benzyl alcohol in CH2Cl2 or CH3CN caused an aldol-type reaction to produce 4-substituted 4-benzyloxybutan-2-ones in high yields.Use of methanol instead of benzyl alcohol produced not only 4-methoxybutan-2-one but also 3-buten-2-one by dehydromethoxylation.

Crossed aldol-type reactions catalyzed by rhodium complexes

Crossed aldol-type reactions of enol trimethylsilyl ethers with aldehydes and ketones are smooth when carried out with a catalytic amount of a rhodium complex, Rh4(CO)12 or X (X=PF6 and ClO4; COD=cycloocta-1,5-diene, DPPB=1,4-bis(diphenylphosphino)butane), under neutral conditions.A suitable catalyst enables the isolation of three different types of aldol reaction product, β-trimethylsiloxy ketones, β-hydroxy ketones, and α,β-unsaturated ketones.Rh4(CO)12 and ClO4 also catalyze the reaction of enol trimethylsilyl ethers with acetals or ketals, whereas PF6 does not.When ClO4 is used as the catalyst, this type of aldol reaction is extended to the one-pot synthesis of trisubstituted furans from enol trimethylsilyl ether and α-trimethylsiloxy acetal.

ALDOL-TYPE REACTIONS BETWEEN TRIMETHYLSILYL ENOL ETHERS AND ACETALS WITH THE AID OF RHODIUM COMPLEX

Aldol type reactions of trimethylsilyl enol ethers with acetals, ketals and orthoesters are successfully performed with the aid of a catalytic amount of rhodium complex Rh4(CO)12 or (Rh(COD)(DPPB))(1+)*ClO4(1-), under neutral conditions.

ACETYL FLUOROSULFONATE - GENERATION FROM ACETYL FLUORIDE AND SULFUR TRIOXIDE AND REACTIONS WITH OLEFINS

The acylation of methylenecyclobutane, styrene, and vinylcyclopropane by acetyl fluorosulfonate, generated in situ from acetyl fluoride and sulfur trioxide, followed by treatment with methyl or propyl alcohols leads to the products from conjugate addition (alkoxy ketones) in addition to elimination products (α,β-unsaturated ketones).The employed methods makes it possible to separate the stages of addition of the acetyl group and the external nucleophile through the intermediate formation of covalently bonded alkyl fluorosulfonates.