221676-47-7

Upstream product

• 4784-77-4 (E/Z)-crotyl bromide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 35998-93-7 tri-n-butylcrotyltin 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 66534-32-5 α,α-diisopropyl-β-methylhomoallylic alcohol 
• 6117-91-5 (E/Z)-2-buten-1-ol 
• 591-97-9 1-chloro-2-butene 
• 504-61-0 (E)-but-2-enol 
• 598-32-3 2-hydroxy-3-butene 
• 1357478-15-9 (±)-2-(but-3-en-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 

Downstream Products

• 122293-82-7 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-1-cyclohexyl-2-methyl-but-3-enyl ester 
• 122405-35-0 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-1-cyclohexyl-2-methyl-but-3-enyl ester 
• 1357478-32-0 (1S,2S)-1-cyclohexyl-2-methylbut-3-en-1-yl phenylcarbamate 
• 94453-45-9 (R,Z)-1-cyclohexylpent-3-en-1-ol 
• 94453-46-0 1-cyclohexylpent-3-en-1-ol 
• 370581-89-8 5-cyclohexyl-5-hydroxy-pent-2-enoic acid ethyl ester 
• 201854-40-2 1-phenyl-hept-5-en-3-ol 
• 294675-18-6 1-cyclohexyl-pent-3-en-1-ol 

Relevant academic research and scientific papers

A new mechanistic proposal for the origin of α-homoallylic alcohols in indium-mediated allylation reactions in water

A new mechanism is proposed for the α-regioselective indium-mediated allylation reaction in water. Based on the results and observations obtained from an NMR study, a cross-over experiment and the complete inversion of the stereochemistry of 22β γ-adduct

Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation, and Crotylation of Aldehydes

In this study, we disclose the catalytic addition of bi(cyclopentyl)diol-derived boronates to aldehydes promoted by chiral phosphoric acids, allowing for the formation of enantioenriched homoallylic, propargylic, and crotylic alcohols (up to >99% enantiom

Cooperative titanocene and phosphine catalysis: Accelerated C-X activation for the generation of reactive organometallics

The study presented herein describes a reductive transmetalation approach toward the generation of Grignard and organozinc reagents mediated by a titanocene catalyst. This method enables the metalation of functionalized substrates without loss of functional group compatibility. Allyl zinc reagents and allyl, vinyl, and alkyl Grignard reagents were generated in situ and used in the addition to carbonyl substrates to provide the corresponding carbinols in yields up to 99%. It was discovered that phosphine ligands effectively accelerate the reductive transmetalation event to enable the metalation of C-X bonds at temperatures as low as -40 °C. Performing the reactions in the presence of chiral diamines and amino alcohols led to the enantioselective allylation of aldehydes.

Chiral zinc-catalyzed asymmetric α-alkylallylation and α-chloroallylation of aldehydes

Two birds with one stone: In the presence of Zn(OH)2 and a chiral bipyridine ligand, racemic α-substituted allylboronates 2 reacted with aldehydes 1 (see scheme) exclusively in an α-addition fashion to afford various homoallylic alcohols 3 bear

Gallium-mediated allyl transfer from bulky homoallyl alcohol to aldehydes or alkynes: Control of dynamic σ-allylgalliums based on retro-allylation reaction

A new method for the preparation and control of dynamic σ-allylgalliums is disclosed. Upon treatment with a Grignard reagent and gallium trichloride, bulky homoallyl alcohols undergo gallium-mediated retro-allylation reaction to provide σ-allylgallium reagents. The σ-allylgallium reagents generated were applied to carbonyl allylation. The retro-allylation reaction generates (Z)- and (E)-σ-crotylgalliums stereospecifically, starting from erythro- and threo-homoallyl alcohols, respectively. The stereochemically defined crotylgallium reagents effected stereoselective allylation of aldehydes. Allylgallation reaction of alkynes with the allylgallium reagents prepared by retro-allylation is also described.

Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols

Under catalysis of Pd(OAc)2-(P-n-Bu)3, Et 2Zn promotes a variety of allyl alcohols to undergo nucleophilic allylation of aliphatic aldehydes and ketones at room temperature and provides homoallyl alcohols in 60-90 and ca. 60% isolated yield, respectively. The reaction is irreversible and kinetically controlled, and unique regio- and stereoselectivities observed for the allylation with unsymmetrically substituted allyl alcohols are discussed.

Iridium-catalyzed carbonyl allylations by allylic alcohols with Tin(II) chloride

Iridium complex [IrCl(cod)]2 can function as a catalyst for the allylation of aldehydes and ketones by allylic alcohols upon addition of an equimolar amount of SnCl2 in THF-H2O; the reaction is carried out between room temperature and 50 °C to give the corresponding homoallylic alcohols. Georg Thieme Verlag Stuttgart.

Carbonyl allylations by allylic chlorides utilizing a reduction of tin(IV) iodide to triiodostannate(II) species with iodide sources

Carbonyl allylations by allylic chlorides either with tin(IV) iodide and tetrabutylammonium iodide (TBAI) in dichloromethane or with tin(IV) iodide and sodium iodide in 1,3-dimethylimidazolidin-2-one at room temperature produced the corresponding homoallylic alcohols. The carbonyl allylations probably proceeded via the reduction of tin(IV) iodide to triiodostannate(II) species with iodide sources such as TBAI and NaI, which led to the construction of a tin(IV)-catalytic cycle based on regeneration of tin(IV) iodide via the transmetalation of homoallyloxytriiodotin to homoallyloxytrimethylsilane with iodotrimethylsilane.

Rhodium-catalyzed carbonyl allylations by allylic alcohols with tin(II) chloride

Rhodium complexes such as [RhCl(cod)]2, [Rh(cod) 2]BF4, and [Rh(cod)(CH3CN)2]BF 4 function as catalysts for carbonyl allylations by allylic alcohols with 1 equimolar amount of tin(II) chlor

Direct preparation of allylic indium(III) reagents from allylic alcohols via a reductive transmetalation of π-allylnickel(II) with indium(I) iodide

InI-mediated direct allylation of carbonyl compounds with allylic alcohols proceeded smoothly with catalytic amounts of Ni(acac)2 and PPh 3 to give the corresponding homoallylic alcohols in high yields. Allylindium compounds were shown to be the real allylating agents in the present system. Substituted allylic alcohols gave branched homoallylic alcohols with syn-selectivity irrespective of the geometry of the starting allylic alcohols, whereas high anti-selectivity was observed when a bulky substituent is present in the allylic alcohols. The outcome of the diastereoselectivity is discussed on the basis of the reaction mechanism, comparing with the corresponding Pd-catalyzed version. Another distinct behavior between the Ni- and Pd-catalyzed allylation was demonstrated in the reaction of hex-1,5-diene-3,4-diol derivatives: the Pd catalyst did not give any coupling product, whereas the Ni-catalyzed InI-mediated reaction with benzaldehyde afforded the 1:1 and 1:2 adduct diols selectively depending on the reaction conditions.