85656-22-0

Upstream product

• 66534-82-5 3-tert-butyl-2,2,4-trimethyl-hex-5-en-3-ol 
• 98-86-2 acetophenone 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 98-83-9 isopropenylbenzene 
• 4894-61-5 trans-but-2-enyl chloride 
• 75851-67-1 4,4,5,5-tetramethyl-2-(1-methyl-2-propenyl)-1,3,2-dioxaborolane 
• 591-97-9 1-chloro-2-butene 
• 4784-77-4 (E/Z)-crotyl bromide 
• 106-99-0 buta-1,3-diene 
• 52884-09-0 (2SR,3RS)-3-methyl-2-phenylpent-4-yn-2-ol 
• 33997-62-5 crotyltris(diethylamino)titanium 
• 83173-81-3 (CH₃CHCHCH₂Ti(OCH(CH₃)2)3) 
• 702-04-5 crotyl phenyl sulfide 

Relevant academic research and scientific papers

Indium(I) iodide-catalyzed regio- and diastereoselective formal α-addition of an α-methylallylboronate to N-acylhydrazones

Indium(I) iodide was found to catalyze the formal α-addition of an α-methylallylboronate to various N-acylhydrazones, in the presence of an alcohol additive, to afford the corresponding anti-α-adducts with high regio- and diastereoselectivity in high yiel

Indium-mediated allylation of carbonyl compounds in deep eutectic solvents

This study describes, for the first time, the in situ generation of indium organometallic reagents in environmentally friendly deep eutectic solvents (DESs). The allylation process of different carbonyl compounds is achieved mediated by indium metal and u

Direct use of 1,3-dienes for the allylation of ketones: Via catalytic hydroindation

In this study, in situ catalytically generated allylic indium from 1,3 dienes and InCl2H was developed for use in the allylation of ketones. This protocol resulted in the unprecedented establishment of a successive combining of quaternary C-C b

[bmim][Br] as an Inexpensive and Efficient Medium for the Barbier-Type Allylation Reaction Using a Catalytic Amount of Indium: Mechanistic Studies

Barbier-type allylation reactions of aldehydes and ketones have been carried out with both unsubstituted and γ-substituted allyl bromides using only a catalytic amount (0.1 equiv.) of In metal in [bmim][Br], but not in H2O, organic solvents, or

Catalytic use of zinc amide for transmetalation with allylboronates: General and efficient catalytic allylation of carbonyl compounds, imines, and hydrazones

The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (～0.1mol%). A mechanistic study revealed that transmetalation was a rate-determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands. Copyright

Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Facile formation of allylzinc species from allylboronate and zinc amide was discovered. The boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, which were successfully employed in catalytic allylation reactions with electrophiles. Asymmetric catalysis using a chiral zinc amide is also reported.

Titanocene(III)-promoted Barbier-type crotylation of carbonyl compounds

A mild, highly regio-and stereoselective method for the crotylation of aldehydes and ketones mediated/catalyzed by titanocene(III) is described. Optimized conditions permit the selective generation of γ-adducts in high yields together with high stereoselectivity, with a predominance of anti stereoisomers.

Regio- and stereoselective preparation of highly substituted tertiary homoallylic alcohols

The titanocene(II)-promoted reaction of α-(benzyldimethylsilyl) allylic sulfides with ketones proceeded with high regio- and stereoselectivity to give δ-silylhomoallylic alcohols. The following palladium catalyzed cross-couplings with organic halides prod

Allyl transfer to aldehydes and ketones by Bronsted acid activation of allyl and crotyl 1,3,2-dioxazaborolidines

Alkyl dioxazaborolidines are air-stable and often crystalline organoboranes. A variety of Bronsted acids activate allyl dioxazaborolidines to generate reactive allyl-transfer reagents in situ. These reagents add to aldehydes and ketones to generate the corresponding alcohols in good yields under mild conditions. The E- and Z-crotyl reagents react diastereoselectively with aldehydes and ketones to produce anti and syn adducts, respectively, a result consistent with a cyclic transition state (type I mechanism).

Preparation of syn -Tertiary homoallylic alcohols utilizing allenyltitanocenes generated by reductive titanation of γ- Trimethylsilylpropargylic carbonates

Figure presented syn-Tertiary homoallylic alcohols were obtained by the reaction of α-silylallenyltitanocenes generated by the reductive titanation of γ-silylpropargylic carbonates with Cp2Ti[P(OEt) 3]2 with ketones and fo