56949-94-1

Upstream product

• 623-43-8 crotonic acid methyl ester 
• 100-52-7 benzaldehyde 
• 1117-71-1 methyl-4-bromo-2-butenoate 
• 71-43-2 benzene 
• 3724-55-8 methyl but-3-enoate 
• 1117-71-1 methyl 4-bromocrotonate 
• 186581-53-3 diazomethane 
• 69637-13-4 2-[hydroxy(phenyl)methyl]but-3-enoic acid 
• 3724-65-0 2-butenoic acid 
• 119582-47-7 tert-butyl((1-methoxybuta-1,3-dien-1-yl)oxy)dimethylsilane 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 29943-38-2 2-methoxycarbonyl-1-methylethyl phenyl sulfide 
• 107-93-7 (E)-but-2-enoic acid 

Downstream Products

• 72853-48-6 (E)-Methyl 2-(phenylhydroxymethyl)-2-butenoate 
• 154073-05-9 methyl 2-phenyl-2,5-dihydro-3-furancarboxylate 

Relevant academic research and scientific papers

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.

Total regio- and diastereocontrol in the aldol reactions of dienolborinates

It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive α-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of an aldol reaction in the presence of a phosphine-borane adduct is also reported.

Oxazaborolidinone-promoted vinylogous mukaiyama aldol reactions

δ-Hydroxy-α,β-unsaturated carbonyl compounds were prepared in one step via the vinylogous Mukaiyama aldol reactions with O,O-silyl ketene acetals. Isopropyl alcohol as additive and tryptophane-based B-phenyloxazaborolidinone were required for obtaining th

P(RNCH2CH2)3N-catalyzed 1,2-addition reactions of activated allylic synthons

Activated allylic compounds of the type RCH:CHCH2Z (Z = CN, CO2Me) react efficiently with aromatic aldehydes in the presence of 20-40 mol % of P(R′NCH2CH2)3N at -94 to -63 °C. Both R = H and R = Me le

An efficient approach to (E)-β-methyl Baylis-Hillman adducts via indium-mediated allylation of aldehydes in aqueous media

A new method has been developed for the synthesis of (E)-β-methyl Baylis-Hillman adducts with high E-Z (>93%) selectivity in modest to good yields. The process consists of two steps: an indium-mediated allylation reaction and a simple base-catalyzed isomerization step. Various aldehydes were allylated with allyl bromides using indium under very mild conditions in aqueous media. The allylation reactions of aromatic and aliphatic aldehydes were largely accelerated by the presence of HCl.

Indium mediated allylation and propargylation reactions of dimethyl acetals and ketals

Indium mediated allylation and propargylation reactions of acetals and ketals with various allyl or propargyl bromides in aqueous media successfully provided the corresponding homoallylic or homopropargylic (and allenylic) alcohol, respectively, in moderate to good yields. Highly chemoselective allylation is also described. The ketal and aryl acetal could be selectively allylated over the aliphatic one in 80-84% yields.

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.

The conjugate addition-aldol tandem reaction of α,β-unsaturated esters catalyzed by lithium benzenethiolate

Reactions of α,β-unsaturated esters with aldehydes were catalyzed by 0.2 equiv of lithium benzenethiolate in the presence of phenyl trimethylsilyl sulfide to afford the conjugate addition-aldol tandem reaction products in the anti stereoselectivity and go

Excellent Aldehyde and Ketone Selectivity in Chromium(II)-Mediated Reformatsky Reactions

The chromium Reformatsky reaction allows the highly chemoselective addition of ester enolates to aldehydes or methyl ketones at room temperature. Aldehyde selectivities of ≥ 50 : 1 vs. methyl ketones and ≥ 200 : 1 vs. larger ketones and other electrophile

Active metals prepared in liquid ammonia. Zinc and tin-promoted synthesis of β-hydroxyesters, homoallylic and homopropargylic alcohols

Active zinc and tin provider can be prepared by reduction of ZnCl2 and SnCl2 with sodium in tetrahydrofuran-liquid ammonia mixtures of various compositions. The activity of the reduced zinc depends on concentration of ammonia in the reactors medium Zinc(A) prepared in liquid ammonia (Method A) was much less active then zinc (B) prepared in THF containing 10-20 volume% of liquid ammonia (Method B). The X-ray powder difractiometry data suggested that zinc (H) was less crystalline then zinc (A). The Reformatsky and Barbier type reactions of carbonyl compounds with α-bromoesters, allylic and propargylic bromides in the presence of Zn or Sn prepared by method B gave the corresponding β-hydroxyesters, homollylic and homopropargylic alcohols in good to excellent yields.