94453-45-9

Upstream product

• 31197-41-8 crotyltributylstannane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 66534-32-5 α,α-diisopropyl-β-methylhomoallylic alcohol 
• 19781-52-3 2,3-dimethylpent-4-en-2-ol 
• 286-45-3 8-oxabicyclo[5.1.0]octane 
• 75851-67-1 4,4,5,5-tetramethyl-2-(1-methyl-2-propenyl)-1,3,2-dioxaborolane 
• 4784-77-4 (E/Z)-crotyl bromide 
• 35998-94-8 (Z)-crotyltri-n-butylstannane 
• 69611-01-4 (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 221676-47-7 1-cyclohexyl-2-methyl-but-3-en-1-ol 

Downstream Products

• 130276-77-6 Bromomethyl-((Z)-(S)-1-cyclohexyl-pent-3-enyloxy)-dimethyl-silane 
• 130276-73-2 (4S,6S)-6-Cyclohexyl-4-ethyl-2,2-dimethyl-[1,2]oxasilinane 
• 130276-79-8 (1S,3S)-1-Cyclohexyl-3-ethyl-butane-1,4-diol 

Relevant academic research and scientific papers

BuSnCl3 Mediated Z-Selective 2-Butenylation and erythro-Selective 1-Methyl-2-propenylation of Aldehydes by 1-(Tributylstannyl)-2-butene

Butyltin trichloride mediated reaction of 1-(tributylstannyl)-2-butene with aldehydes is described.This reaction is useful as a stereoselective method for (Z)-2-butenylation and erythro-1-methyl-2-propenylation of aldehydes.

Epoxide as an aldehyde equivalent in allyl-transfer reaction with γ-adduct of homoallylic alcohol (allyl donor) giving α-adduct of homoallylic alcohol

Acid-catalyzed reactions of epoxides 2 with homoallylic alcohol γ-adducts, 1 [Me2C(OH)CHRCH{double bond, long}CH2], afford homoallylic alcohol α-adducts 3-5 via allyl-transfer reaction, sometimes being more effective than those using

Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A

Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three-component allylboration-Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % ove

Highly stereoselective synthesis of z-homoallylic alcohols by kinetic resolution of racemic secondary allyl boronates

α to Z: Racemic α-chiral allyl boronates, which are readily synthesized from the respective primary allyl halides, undergo a highly efficient kinetic resolution in a face- and Z-selective allylation of aldehydes catalyzed by the chiral Bronsted acid (R)-TRIP (see scheme; Epin=tetraethylethylene glycol). Copyright

Crotylation of aldehydes by crotyltins: Discrimination between mechanisms involving transmetallation or simple lewis acid assistance through the consideration of the stereochemistry of the corresponding homoallylic alcohols

In the reaction of crotyltins with aldehydes in the presence of metal salts, the double consideration of the syn/anti ratio of the branched homoallylic alcohols and the Z/E ratio of their linear regioisomers is proposed as a way to discriminate between a reaction mechanism involving a transmetallation step and a reaction mechanism involving simple Lewis acid activation of the aldehyde. The formation of branched syn isomers along with Z-linear isomers as major compounds is considered to be indicative of a reaction occurring under Lewis acid assistance, whereas preference for the branched anti isomers together with E-linear isomers is considered to be indicative of a transmetallation step prior to crotylation. For reactions performed in the presence of CeCl3·7H2O/NaI, the Lewis acid assistance was shown to be the exclusive or highly prevalent pathway. Moreover, in regards to the selectivity, the regiopreference depends on the nature of the crotyltin. Whereas soluble crotyltin preferentially leads to Z-linear adducts, polymer-supported crotyltin affords the syn-branched adducts probably due to a lower 1,3-metallotropy. For reactions performed in the presence of InX 3, simple Lewis acid assistance and transmetallation appear to be competitive processes; the first one is favoured with aromatic aldehydes especially in dichloromethane, whereas transmetallation appears to be prevalent with poorly reactive aldehydes especially with InBr3 in acetonitrile. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of 4-substituted homoallylic alcohols via a one-pot tandem Lewis-acid catalyzed crotylboration-[3,3]-sigmatropic rearrangement

Crotylboration of aldehydes with E- or Z-crotylboronates in the presence of catalytic amounts of indium triflate provides the corresponding 4-substituted homoallylic alcohols. The Royal Society of Chemistry 2005.

Allylation of aldehydes promoted by the cerium(III) chloride heptahydrate/sodium iodide system: The dependence of regio- and stereocontrol on the reaction conditions

The cerium(III) chloride heptahydrate/sodium iodide complex (CeCl 3·7 H2O/NaI) acts as a useful promoter in the carbon-carbon bond forming reaction by addition of allyltributylstannanes to aldehydes. The reaction of 2-butenyltributyl

A novel preparation of allylic trichlorotins from α,α-diisopropylhomoallylic alcohols and its application to carbonyl allylations

α,α-Diisopropylhomoallylic alcohols react with tin(II) chloride and NCS in CH2Cl2 at -40 °C to -60 °C to produce allylic tins and diisopropyl ketone, and the allylic tins in situ cause nucleophilic addition to aldehydes to afford α-s

Development of a highly α-regioselective indium-mediated allylation reaction in water

Linear α homoallylic alcohol adducts were obtained with high regioselectivities in moderate to good yields using allylic indium reagents in the presence of 10 M water. The exceptionally high regioselectivities observed were neither steric nor electronic i

The first In(OTf)3-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols

A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.