69637-13-4

Upstream product

• 13991-36-1 4-bromocrotonic acid 
• 100-52-7 benzaldehyde 
• 625-38-7 but-3-enoic acid 
• 109751-81-7 4-trimethylsilyl-2-butenoate trimethylsilyl ester 
• 13991-36-1 4-bromocrotonic acid 
• 3724-65-0 2-butenoic acid 
• 106-95-6 allyl bromide 
• 87121-06-0 1,1-bis(trimethylsilyloxy)-buta-1,3-diene 
• 13688-54-5 3-butenoictrimethylsilylester 

Downstream Products

• 154073-05-9 methyl 2-phenyl-2,5-dihydro-3-furancarboxylate 
• 56949-94-1 methyl threo-2-(1-hydroxy-1-phenylmethyl)-3-butenoate 
• 56949-94-1 methyl erythro-2-(1-hydroxy-1-phenylmethyl)-3-butenoate 

Relevant academic research and scientific papers

SILYLCETENES ACETALS ISSUS D'ACIDES α,β-ETHYLENIQUES: PREPARATIONS ET APPLICATIONS EN SYNTHESE

The preparation of bis(trimethylsilyl)butadienyl acetal(I) and bis(trimethylsilyl)methylbutadienyl acetal (II) is reported; compound I reacts with phenyl aldehyde and titanium chloride to give linear and branched isomers of hydroxyacids.

SUR LA REGIO SPECIFICITE DE LA REACTION DE REFORMATSKY APPLIQUEE AU γ-BROMOCROTONATE ET AU γ-BROMOSENECIOATE DE TRIMETHYLSILYLE

The regiospecificity of Reformatsky reactions of γ-bromocrotonic and γ-bromosenecioic timethylsilyl esters are discussed.One-step reactions lead to a majority of α-substituted derivatives, while in two-step reactions, the γ-substituted products are obtain

Synthesis of α-alkenyl-β-hydroxy adducts by α-addition of unprotected 4-bromocrotonic acid and amides with aldehydes and ketones by chromium(II)-mediated reactions

The regioselective and diastereoselective chromium(II)-mediated reactions of 4-bromocrotonic acid or amides with aldehydes and ketones can proceed without the need to protect protic sites to generate the respective α-alkenyl-β-hydroxy adducts, i.e. formally the addition of the α-anion of a carboxylic acid or amide to an oxo-compound is featured.

Indium-mediated addition of 4-bromocrotonic acid to aldehydes and ketones-A simple, high yielding route to αallyl-β-hydroxy carboxylic acids

We report a simple procedure for the indium-mediated addition of 4-bromocrotonic acid to a variety of aldehydes and ketones. In all instances the reaction proceeds exclusively with α-addition and typically in moderate to good yields (42-100%). The effect

Exclusive α-coupling in the aldol reaction of unsaturated trimethylsilyl esters: An efficient and practical direct synthesis of unsaturated β-hydroxy acids

The lithium enolates of trimethylsilyl but-3-enoate and 3-methylbut-3-enoate reacted with aldehydes and saturated or aromatic ketones at -70°C to give exclusively the α-condensation products in excellent yields. The unsaturated β-hydroxy acids thus obtained were directly identified, and the usual conversion into their methyl esters with diazomethane was not necessary. Unsaturated ketones underwent Michael reaction through α-addition leading to the unsaturated 5-oxo acids.

Catalytic oxyselenenylation-deselenenylation reactions of alkenes - Stereoselective one-pot conversion of 3-alkenols into 2,5-dihydrofurans

A stereoselective multi-step one-pot procedure for converting 2- methoxycarbonyl-3-alkenols into 3-methoxycarbonyl-2,5-dihydrofurans, using only catalytic amounts of diphenyl diselenide and an excess of ammonium persulfate, has been developed. The erythro alkenols give the trans dihydrofurans, while the threo stereoisomers give the corresponding cis products. The configurations of the starting alkenols were deduced from those of the intermediate phenylseleno tetrahydrofurans, which were independently obtained from reactions of the alkenols with stoichiometric amounts of phenylselenenyl sulfate.

Dienediolates from Unsaturated Carboxylic Acids. Reaction with para-Substituted Benzaldehydes. Electronic Effects on Regioselectivity

Regioselectivity α/γ ratios for addition of the lithium dienediolate of crotonic acid to para-substituted benzaldehydes are subject to small electronic effects when reactions are carried out at low temperature, but strong influence by substituents is observed on heating for 1 h at 60 deg C.A linear correlation is then found between regiochemical ratios and ?p parameters.Stereoselectivity RR/RS ratios (33:66 to 43:57) for α-adducts obtained in the cold do not depend on the substituents.

Bis(trimethylsiloxy)-1,1 butadiene-1,3 et trimethylsilyl-4 butene-2 oate de trimethylsilyle: preparations et reactions avec benzaldehyde

The preparation of 4-trimethylsilyl-2-butenoate trimethylsilyl ester and 1,1-bis(trimethylsiloxy)-1,3-butadiene are described.The latter silyl derivative reacts with benzaldehyde in the presence of ZnBr2 in THF to give exclusively γ-substituted product (E configuration) in high yield.The fluoride ion catalyzed reaction affords predominantly α-alkylated compounds.

SUR LA REACTION DE PREFORMATSKY. PREPARATION ET REACTIVITE DE L'ORGANOZINCIQUE ISSU DU SEL BROMOZINCIQUE DE L'ACIDE γ-BROMOCROTONIQUE

The condensation of aldehydes and ketones with the bromozinc salt derived from γ-bromocrotonic acid, in the presence of zinc, yield to the "linear" and "branched" unsaturated hydroxyacids.These latters, which represent the kinetic products of the reaction, equilibrate at the alcoholate state to give, after hydrolysis, the "linear" compounds.