113501-08-9

Upstream product

• 542-75-6 E/Z-1,3-Dichloropropene 
• 100-52-7 benzaldehyde 
• 18083-15-3 3-chloroallyltrichlorosilane 
• 107-05-1 3-chloroprop-1-ene 
• 158813-39-9 2-(Z-3-chloroprop-2-enyl)-4,4,5,5-tetramethyl-1,2,3-dioxaborolane 
• 88086-59-3 1-chloro-3-iodoprop-1(Z)-ene 

Downstream Products

• 21699-63-8 cis-2-phenyl-3-ethenyl oxirane 
• 182210-51-1 cis-(1R,2S)-1,2-epoxy-1-phenyl-3-butene 
• 182210-57-7 cis-(1S,2R)-1,2-epoxy-1-phenyl-3-butene 
• 21699-64-9 trans-2-phenyl-3-ethenyl oxirane 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 

Relevant academic research and scientific papers

Indium-mediated reaction of 1,3-dichloro- and 1,3-dibromopropenes with carbonyl compounds. Generation of novel 3,3-diindiopropene

Indium-mediated reaction of 1,3-dichloropropene with aldehyde gave syn-chlorohydrin predominantly. A similar reaction of 1,3-dibromopropene gave vinyloxirane and homoallyl alcohol; the former is formed from γ-bromoallylindium via the corresponding bromohydrin, and the latter is considered to be derived from a unique allylic diindium reagent, 3,3-diindiopropene.

Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis

Olefin metathesis has had a large impact on modern organic chemistry, but important shortcomings remain: for example, the lack of efficient processes that can be used to generate acyclic alkenyl halides. Halo-substituted ruthenium carbene complexes decompose rapidly or deliver low activity and/or minimal stereoselectivity, and our understanding of the corresponding high-oxidation-state systems is limited. Here we show that previously unknown halo-substituted molybdenum alkylidene species are exceptionally reactive and are able to participate in high-yielding olefin metathesis reactions that afford acyclic 1,2-disubstituted Z-alkenyl halides. Transformations are promoted by small amounts of a catalyst that is generated in situ and used with unpurified, commercially available and easy-to-handle liquid 1,2-dihaloethene reagents, and proceed to high conversion at ambient temperature within four hours. We obtain many alkenyl chlorides, bromides and fluorides in up to 91 per cent yield and complete Z selectivity. This method can be used to synthesize biologically active compounds readily and to perform site- and stereoselective fluorination of complex organic molecules.

Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes

Isomerically pure trans-and cis-γ-bromoallyltrichlorosilanes 4 and 5 have been synthesized and shown to react with aromatic aldehydes 1 in the presence of Lewis-basic catalysts (e.g., DMF) to produce the corresponding anti-and syn-allylbromohydrins 8 and 9, respectively, as single diastereoisomers. With BINAPO 25 as a chiral catalyst, promising enantioselectivity (≤50% ee) has been attained.

Cr(Salen)-catalyzed addition of 1,3-dichloropropene to aromatic aldehydes. A simple access to optically active vinyl epoxides.

[reaction: see text]. Chiral Cr(Salen) complex (1) prepared in situ from CrCl3 promotes the enantioselective addition of 1,3-dichloropropene to aromatic aldehydes in the presence of Mn as the stoichiometric reductant and Me3SiCl as a scavenger. The result

Either γ-syn- Or γ-anti-selective palladium-catalysed carbonyl allylation by mixed (E)- and (Z)-l,3-dichloropropene with tin(II) halides

Palladium-catalysed carbonyl allylations by mixed (E)- and (Z)-1,3-dichloropropene with SnI2-Bu4NI and SnCl2 diastereoselectively produce syn and anti 1-substituted 2-chlorobut-3-en-1-ols, respectively. These are transform

Chloroallyl Anion: Highly Regio- and Diastereoselective α-Addition of Chloroallyl Zinc Reagent to Carbonyl Compounds

The chloroallyl zinc reagent generated insitu by deprotonation of allyl chloride in the presence of lithium diisopropylamide and zinc chloride undergoes highly regio- and diastereoselective α-addition to carbonyl compounds to give syn chlorohydrins which

A SIMPLE, STEREOSELECTIVE, ROOM-TEMPERATURE SYNTHESIS OF CIS VINYLOXIRANES AND TRANS 1-PHENYL-1,3-BUTADIENE

The organotin reagent from 1-chloro-3-iodoprop-1-ene and SnCl2 in dimethylformamide reacted with aldehydes by its chlorine-substituted carbon atom.Treatment with NaOMe then gave cis vinyloxiranes with good stereoselectivity.Benzaldehyde and 1-bromo-3-iodo