40596-17-6

Upstream product

• 300-57-2 allylbenzene 
• 78-84-2 isobutyraldehyde 
• 4392-24-9 Cinnamyl bromide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 75-11-6 diiodomethane 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 103-54-8 cinnamyl acetate 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 74785-32-3 (E)-cinnamyl(tributyl)tin 
• 100009-29-8 (E)-1-tert-butyldimethylsilyloxy-3-phenyl-2-propene 
• 673-32-5 1-Phenylprop-1-yne 
• 78-83-1 2-methyl-propan-1-ol 
• 960-16-7 tributylphenylstannane 
• 40596-17-6 (3RS,4RS)-2-methyl-4-phenyl-5-hexen-3-ol 

Downstream Products

• 40596-17-6 (3R,4S)-2-Methyl-4-phenyl-hex-5-en-3-ol 

Relevant academic research and scientific papers

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α, γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.

Diethylzinc-mediated allylation of carbonyl compounds catalyzed by [(NHC)(PR3)PdX2] and [(NHC)Pd(η3-allyl)Cl] complexes

[(NHC)(PR3)PdX2] complexes (NHC = N-heterocyclic carbene) are active precatalysts in the palladium-catalyzed allylation of carbonyl compounds with allylic acetates and diethylzinc. A comparative study examining the catalytic activity of a series of six of these complexes was carried out with allyl and cinnamyl acetates. [(IMeSMe)(PPh3)PdI 2] was found to be the most versatile precatalyst (IMesMe = 1-mesityl-3-methylimidazol-2-ylidene) and the scope of the reaction was investigated with this complex. [(IMeSMe)(PPh3)-PdI2] catalyzes the allylation of aromatic (except 4-nitrobenz-aldehyde) and aliphatic aldehydes (including enolizable aldehydes) with cinnamyl acetate to give the corresponding homoallylic alcohols in 57-98 % yields and dlastereoselectivities ranging from 70:30 to 92:8. The allylation of acetone also takes place under the same conditions, leading to the expected adduct in 63 % yield. The reaction with cyclohexenyl acetate proceeds at room temperature to afford the homoallylic alcohols in 40-78% yields with excellent diastereoselec-tivities (>98:2), but is limited to aromatic aldehydes. An experimental study concerning the mechanism, of the transformation was also carried out. We first demonstrated that the phosphane ligand was not essential for the reaction to take place. [(NHC)Pd(allyl)Cl] complexes are active precatalysts and lead to similar yields in the presence or in the absence of PPh3. Transmetalation of [(NHC)Pd(allyl)Cl] complexes with diethyl- or dimethylzinc, which is a determining step for the mechanism, was studied by 1H NMR spectroscopy. The reaction of [(IPr)Pd(allyl)Cl] with dimethylzinc affords rapidly [(IPr)Pd(η3-allyl)(Me)] but no detectable trace of allylzinc species [IPr = 1, 3-bis(2, 6-diisopropylphenyl)imidazol-2-ylidene]. [(IPr)Pd(η3-allyl)(Me)] was found to be a nucleophilic species able to react smoothly at room temperature with an aldehyde in the absence of zinc to form the corresponding homoallylic alcohol.

Iridium-catalyzed coupling reaction of primary alcohols with 1-aryl-1-propynes leading to secondary homoallylic alcohols

We report iridium-catalyzed coupling of 2-alkynes such as 1-aryl-1-propynes with primary alcohols leading to secondary homoallylic alcohols as products. This reaction involves an iridium-catalyzed novel catalytic transformation of 2-alkynes and primary al

Stereoselective [2,3]-sigmatropic rearrangements of unstabilized nitrogen ylides

The steric course of the [2,3]-rearrangement of several unstabilized nitrogen ylides has been investigated. The reactions proceed cleanly through an anti transition state, affording modest to good yields of a single diastereomer of the product. In two exa

Transition-metal-catalyzed sequential cross-coupling of bis(iodozincio)methane and -ethane with two different organic halides

Bis(iodozincio)methane, prepared from diiodomethane and zinc, reacts with an organic halide in the presence of a transition-metal catalyst to give an iodozinciomethylenated compound; this then reacts with another organic halide to form a C-C bond. The overall process connects two electrophiles with one carbon atom. Bis(iodozincio)ethane can also undergo this transformation, yielding a new stereogenic center. The asymmetric induction of this stereogenic center was investigated by using a chiral palladium catalyst.

Reaction of allylic-type diindium compounds with electrophiles

Allylic-type diindium reagents were prepared from 3-bromo-1-iodopropene (1a), 3-bromo-1-iodo-1-phenylpropene (1b), or 2,4-diiodobut-2-en-1-ol (1c) with metallic indium, and their successive coupling with electrophiles was examined. The coupling behavior o

Indium Triiodide (InI3)-Catalyzed Allylation of Carbonyl Compounds by Allylic Tins

Indium triiodide is an effective catalyst for the allylation of aldehydes via the transmetallation with allylic tin compounds. Moreover, the chelation-controlled allylation of α-alkoxyketones proceeded with a catalytic amount of indium triiodide.

Allylic tin(IV)-tin(II) chloride-acetonitrile as a novel system for allylation of carbonyls or imines

Effective allylation of aldehydes, ketones and imines was accomplished by allylic tributyltins 1 in the presence of SnCl2 in an acetonitrile solution. In this reaction system, Sn(IV)-Sn(II) transmetallation must play a key role, generating the

Indium Mediated Coupling of Aldehydes with Allyl Bromides in Aqueous Media. The Issue of Regio- and Diastereo-selectivity

The regio- and diastereo-selectivity in the coupling of γ-substituted allyl bromides with aldehydes mediated by indium in water were found to be dependent on the steric effect of the substituents on both allyl bromides and the aldehydes.