19261-14-4

Upstream product

• 100-52-7 benzaldehyde 
• 4957-34-0 acetic acid 3-bromo-1-propenyl ester 
• 500756-90-1 (E)-3-bromoprop-1-enyl benzoate 
• 52755-39-2 (2E)-1-phenylbut-2-en-1-ol 
• 82238-07-1 erythro-1-phenyl-2-(methoxymethoxy)-3-butenol 
• 85677-20-9 threo-1-phenyl-2-(methoxymethoxy)-3-butenol 
• 1208092-25-4 prop-2-ene-1,1-diyl dibenzoate 
• 62322-46-7 3-(1-methoxy-1-methylethoxy)prop-1-ene 
• 106948-16-7 {Dimethyl-[(R)-1-((S)-phenyl-trimethylsilanyloxy-methyl)-allyl]-silanyl}-diisopropyl-amine 
• 500757-14-2 C₁₇H₁₆O₃ 
• 81656-05-5 2-methoxy-1-phenylbut-3-en-1-ol 
• 591-51-5 phenyllithium 
• 107-02-8 acrolein 

Downstream Products

• 4411-89-6 (E/Z)-2-phenylcrotonaldehyde 
• 37442-55-0 1-phenylbut-3-en-2-one 
• 13995-41-0 4,5-trans-2,2-dimethyl-4-phenyl-5-ethenyl-1,3-dioxolane 
• 13995-41-0 4,5-cis-2,2-dimethyl-4-phenyl-5-ethenyl-1,3-dioxolane 
• 195508-14-6 4-hydroxy-4-phenyl-1-butene-3-one 

Relevant academic research and scientific papers

A new protocol for the acetoxyallylation of aldehydes mediated by indium in THF

matrix presented A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium

Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 in 72-98% yields with >95% ee and >20:1 dr. Application of this method to the synthesis of the tetrafibricin C(23)-C(40) fragment 19 is described.

Diastereo- and enantioselective anti-alkoxyallylation employing allylic gem-dicarboxylates as allyl donors via iridium-catalyzed transfer hydrogenation

(Chemical Equation Presented) Enantioselective transfer hydrogenation of gem-dibenzoate 1e in the presence of aromatic, α,β-unsaturated, or aliphatic aldehydes 2a-i mediated by isopropyl alcohol and employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, 4-cyano-3-nitrobenzoic acid, and (R)-SEGPHOS delivers products of alkoxyallylation 3a-i, 4a, 4e, 4f, and 4i in good isolated yields (62-82%) with good to excellent diastereoselectivities (7:1 to 18:1 dr) and exceptional enantioselectivities (90-99% ee). This protocol provides an alternative to the use of premetalated nucleophiles in carbonyl alkoxyallylation. Copyright

3-bromozinc propenyl esters: An experimental and theoretical study of the unique stereocrossover observed in their addition to aromatic and aliphatic aldehydes

(Chemical Equation Presented) We report the results of a combined experimental and theoretical study on the reaction of 3-bromopropenyl acetate in the presence of zinc with three different aldehydes (i.e., benzaldehyde, 2-methylpropanal, and cyclohexaneca

Synthesis of vinyl 1,2-diketones

A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by 1O2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones.

3-Bromopropenyl esters in organic synthesis: Indium- and zinc-mediated entries to alk-1-ene-3,4-diols

Metallic indium and zinc readily add to 3-bromopropenyl acetate (5) and benzoate (6) either in THF or in water, affording the corresponding 3-acyloxyallyl organometallic compounds. Nucleophilic addition to aldehydes opens a route to alk-l-ene-3,4-diols 2 in good to excellent yields. Two synthetic protocols were developed, the former involving indium in THF under Grignard conditions and the latter involving zinc in aqueous ammonium chloride under Barbier conditions. The diastereo-selectivity, under all the conditions examined, mainly depends on the nature of the carbonyl compound; conjugated aldehydes afford syn adducts 2, while unconjugated aldehydes display the opposite anti stereopreference.

Metalated Allylaminosilane: A New, Practical Reagent for the Stereoselective α-Hydroxyallylation of Aldehydes to Erythro-1,2-diol Skeletons

A zinc reagent derived from allyl(diisopropylamino)dimethylsilane reacts with aldehydes regio- and stereoselectively to form erythro-3-silyl-1-alken-4-ols, which are further transformed into erythro-1-alkene-3,4-diols by hydrogen peroxide oxidation of the

Regiochemical Convergence in the Reaction of Heterosubstituted Allylic Carbanions via Allylic Aluminum and Boron "Ate" Complexes

The regiochemistry in reactions of heterosubstituted allylic carbanions (1) is highly controlled via allylic aluminum or boron "ate" complexes which direct both carbonyl compounds and reactive halides to the α-position with high regioselectivity.For example, carbonyl compounds react with the oxygen- (3), sulfur- (12), selenium- (20), and silicon- (25) substituted allylic carbanions at the α-position via the ate complexes.Although the reactions of the ate complexes (2) with aldehydes generally produce a mixture of erythro and threo isomers, the aluminum ate comlex of 3b gives the erythro isomer (5) with very high stereoselectivity.This procedure is applied to the stereoselective synthesis of exo-brevicomin (9).With allylic halides, the oxygen- (3a) and sulfur- (12) substituted allylic carbanions again react at the α-position via the ate complexes.However, the coupling mode is entirely different; the α-α' coupling product (10) is obtained from 3a, while the α-γ' coupling product (15) is produced from 12.

Stereoselective Acyclic Synthesis via Allylmetals: Vicinal Diols from γ-Alkoxyallylaluminium Compounds and Aldehydes or Ketones

The reaction of in situ generated γ-alkoxyallylaluminium compounds with aldehydes or ketones at -78 deg C leads to the highly diastereoselective formation of mono-protected vicinal diols; the precursor to exo-brevicomin was efficiently synthesised using t