74290-31-6

Upstream product

• 620-23-5 m-tolyl aldehyde 
• 108-59-8 malonic acid dimethyl ester 
• 529-20-4 2-methylphenyl aldehyde 
• 6935-65-5 3,N,N-trimethylbenzamide 

Downstream Products

• 1298068-87-7 dimethyl 2-[3-methyl-1-(3-methylphenyl)but-3-enyl]malonate 
• 1298068-72-0 dimethyl 2-[1-(3-methylphenyl)but-3-enyl]malonate 
• 1355017-69-4 C₁₃H₁₄O₅ 
• 1019650-80-6 4-(3-methylphenyl)pyrrolidin-2-one 
• 79133-32-7 methyl 2-oxo-4-(3-methylphenyl)pyrrolidine-3-carboxylate 

Relevant academic research and scientific papers

Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes

Catalytic enantioselective [4+3] cycloaddition reaction betweeno-quinone methides and oxiranes was achieved by using a chiralN,N′-dioxide/TbIIIcomplex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%)

Electricity Driven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: a Mild and Straightforward Access to β-Hydroxy Ketones

An unprecedented external oxidant-free electrochemical protocol for 1, 3-oxohydroxylation of donor-acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π-electron cloud of the aryl ring to cleave the strained Csp3?Csp3 bond of cyclopropane to afford the β-hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.

Amides as surrogates of aldehydes for C-C bond formation: amide-based direct Knoevenagel-type condensation reaction and related reactions

Aldehydes are perhaps the most versatile compounds that enable many C-C bond forming reactions, which are not amenable for other subclasses of carbonyl compounds. We report the first use of amides as surrogates of aldehydes for C-C bond formation, namely,

Scandium(III) Trifluoromethanesulfonate Catalyzed Selective Reactions of Donor–Acceptor Cyclopropanes with 1,1-Diphenylethanols: An Approach to Polysubstituted Olefins

An unexpected synthetic approach to polysubstituted olefins through the scandium(III) trifluoromethanesulfonate catalyzed ring-opening reaction of donor–acceptor cyclopropanes with 1,1-diphenylethanols was developed. The reactions, which are experimentally easy to handle, feature tolerance of various functional groups and mild reaction conditions. On the basis of experimental evidence, a plausible mechanism was also proposed.

Efficient synthesis of β-aryl-γ-lactams and their resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen

An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)- and (S)-Baclofen hydrochloride.

Triflic Acid Catalyzed Formal [3 + 2] Cycloaddition of Donor-Acceptor Oxiranes and Nitriles: A Facile Access to 3-Oxazolines

A TfOH-catalyzed chemoselective [3 + 2] cycloaddition of donor-acceptor oxiranes and nitriles is described. This reaction provides an efficient and practical method for the preparation of useful 3-oxazolines in good to excellent yields (up to 99%).

Synthesis of 3-Oxazolines via SnCl4-Promoted Formal [3+2] Cycloaddition of Donor-Acceptor Oxiranes and Nitriles

A novel SnCl4-promoted formal [3+2] cycloaddition of donor-acceptor oxiranes and nitriles via chemoselective C-C bond breakage was developed. This reaction provides an efficient and practical method for the preparation of 3-oxazolines in good yields (up to 89%).

TiCl4 promoted formal [3 + 3] cycloaddition of cyclopropane 1,1-diesters with azides: Synthesis of highly functionalized triazinines and azetidines

A TiCl4 promoted formal [3 + 3] cycloaddition of cyclopropane 1,1-diesters with azides has been developed for the synthesis of highly functionalized triazinines. Both stoichiometric and substoichiometric versions of this reaction were accomplished dependent on the choice of solvent. It is noteworthy that the corresponding products could be easily converted to biologically important azetidines by simple thermolysis.

C-O versus C-C bond cleavage: Selectivity control in Lewis acid catalyzed chemodivergent cycloadditions of aryl oxiranyldicarboxylates with aldehydes, and theoretical rationalizations of reaction pathways

A clean break: Lewis acid catalyzed chemodivergent [3+2] cycloadditions of aryl oxiranyldicarboxylates with aldehydes are revealed, in which the C-C or C-O bond cleavage of oxiranes can be controlled by the use of Ni(ClO 4)2 or Sn(OTf)2 catalysts (see scheme). Possible reaction pathways for these transformations are demonstrated by theoretical calculations. Copyright

Ytterbium-catalyzed conjugate allylation of alkylidene malonates

Alkylidene malonates undergo efficient conjugate allylation upon treatment with allylstannanes or allylsilanes under the action of ytterbium catalysis.