682760-41-4

Upstream product

• 570431-52-6 1-phenylcycloprop-2-ene carboxylic acid methyl ester 
• 22979-35-7 Methyl phenyldiazoacetate 
• 699005-11-3 1-phenyl-2-trimethylsilylcycloprop-2-ene carboxylic acid methyl ester 

Downstream Products

• 682760-57-2 (1-phenylcycloprop-2-en-1-yl)methyl acetate 
• 682760-55-0 [1-[(methoxymethoxy)methyl]-2-cyclopropen-1-yl]-benzene 
• 890003-34-6 (-)-(1S,2R)-(2-methyl-1-phenyl-cycloprop-1-yl)methanol 
• 1256842-13-3 (1-(methoxymethyl)cycloprop-2-en-1-yl)benzene 

Relevant academic research and scientific papers

Directed RhI-Catalyzed Asymmetric Hydroboration of Prochiral 1-Arylcycloprop-2-Ene-1-Carboxylic Acid Derivatives

A full account on rhodium-catalyzed asymmetric, directed hydroboration of functionalized prochiral cyclopropenes affording enantiomerically enriched cyclopropylboronates is reported. The scope and limitations of two alternate directing groups, ester and carboxamide, are evaluated. It was found that hydroboration of esters appeared to be more sensitive to substitution in the aromatic ring of the substrates. Specifically, ortho-halogens were detrimental for diastereo- and enantioselectivity, possibly because of additional coordination with rhodium. In contrast, more Lewis-basic amide directing groups allowed for stronger chelation to the transition metal, leading to consistently high diastereo- and enantioselectivity in hydroboration across a broader range of substrates.

Radical Addition of SF5Cl to Cyclopropenes: Synthesis of (Pentafluorosulfanyl)cyclopropanes

With the goal of accessing yet unknown SF5-cyclopropyl building blocks, the radical addition of SF5Cl to cyclopropenes was investigated. Addition of the SF5 radical occurs regioselectively at the less substituted carbon of cyclopropenes and trans to the m

An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes asC4units

An efficient method has been described to synthesize dicarbonyl functionalized 1,3-dienes by cleaving the CC bond of enaminones with cyclopropenes in the presence of a rhodium catalyst. The acetate-substituted cyclopropenes are judiciously chosen as standardC4units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a CC bond cleavage of the enaminone and insertion of a newC(sp2) source with the formation of two C-C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading, ambient temperature, and a neutral reaction solvent.

Enantioselective Hydrothiolation: Diverging Cyclopropenes through Ligand Control

In this article, we advance Rh-catalyzed hydrothiolation through the divergent reactivity of cyclopropenes. Cyclopropenes undergo hydrothiolation to provide cyclopropyl sulfides or allylic sulfides. The choice of bisphosphine ligand dictates whether the pathway involves ring-retention or ring-opening. Mechanistic studies reveal the origin for this switchable selectivity. Our results suggest the two pathways share a common cyclopropyl-Rh(III) intermediate. Electron-rich Josiphos ligands promote direct reductive elimination from this intermediate to afford cyclopropyl sulfides in high enantio- A nd diastereoselectivities. Alternatively, atropisomeric ligands (such as DTBM-BINAP) enable ring-opening from the cyclopropyl-Rh(III) intermediate to generate allylic sulfides with high enantio- A nd regiocontrol.

Palladium-Catalyzed Living/Controlled Vinyl Addition Polymerization of Cyclopropenes

Despite the various utilities of cyclopropenes (CPEs) in organic synthesis and ring-opening metathesis polymerization (ROMP), their vinyl addition polymerization has been sporadically explored, and the corresponding living/controlled polymerization remain

Synthesis of 1,5-dioxocanes via the two-fold C-O bond forming nucleophilic 4 + 4-cyclodimerization of cycloprop-2-en-1-ylmethanols

An efficient [4 + 4] cyclodimerization of cyclopropenemethanols operating via a two-fold strain release-driven addition of alkoxides across the double bond of cyclopropenes was investigated. This chemo- and diastereoselective transformation provided previ

Enantioselective desymmetrization of cyclopropenes by hydroacylation

We report an enantioselective desymmetrization of cyclopropenes by intermolecular Rh-catalyzed hydroacylation. Cyclopropylketones, bearing quaternary stereocenters, are produced with diastereocontrol (up to >20:1) and excellent enantiomeric excess (up to >99 ee).

Enantioselective, facially selective carbomagnesation of cyclopropenes

Described is the facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes. The process creates up to four stereocenters in a tandem addition/capture sequence that combines three simple materials to give complex and diverse products. The asymmetry is induced by the inexpensive and recoverable ligand (S)-N-methylprolinol. The enantioselectivity (90-98% ee with MeMgCl) is high for a range of cyclopropenes and electrophiles. Importantly, the diastereoselectivity is complementary to that obtained by enantioselective cyclopropanation with aryldiazoacetates. High enantioselectivities are obtained only when methoxide is included in the reaction. Evidence is provided that at least two chiral ligands are involved in the enantioselectivity-determining step. Copyright

Catalytic Enantioselective Hydrostannation of Cyclopropenes

The first examples of catalytic enantioselective hydrostannation of the C=C double bond of cyclopropenes has been demonstrated. This method allows for the efficient synthesis of 2,2-disubstituted cyclopropylstannanes with high degrees of diastereo- and en