600152-48-5

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 37892-71-0 tert-butyllithium 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 152710-05-9 5-phenyl-1-pentyn-3-yl methanesulfonate 

Downstream Products

• 1105596-53-9 C₁₅H₁₉Br 
• 1310059-43-8 4,4-dimethyl-1-phenethyl-2-pentynyl 2-bromoacetate 
• 1310059-26-7 (E)-4-(2,2-dimethylpropylidene)-5-phenethyltetrahydro-2-furanol 
• 308274-37-5 5-Azidocarbonyloxy-7-phenyl-2,2-dimethyl-3-heptyne 
• 1437710-20-7 6,6-dimethyl-1-phenylhept-4-yn-3-one 
• 1437708-99-0 (R)-2-(3-ethyl-6,6-dimethyl-1-phenylhept-4-yn-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1437707-90-8 (S)-2-(3-isopropyl-6,6-dimethyl-1-phenylhept-4-yn-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1437708-71-8 (R)-3-benzyl-6,6-dimethyl-1-phenylhept-4-yn-3-ol 
• 1437708-64-9 (R)-7,7-dimethyl-4-(2-phenylethyl)oct-1-en-5-yn-4-ol 
• 1437708-57-0 (R)-3-cyclopropyl-6,6-dimethyl-1-phenylhept-4-yn-3-ol 
• 1437708-50-3 (S)-3-ethyl-6,6-dimethyl-1-phenylhept-4-yn-3-ol 
• 1437707-97-5 (R)-2,6,6-trimethyl-3-(2-phenylethyl)hept-4-yn-3-ol 
• 1437707-67-9 (S)-6,6-dimethyl-1-phenylhept-4-yn-3-yl-N,N-bis(propan-2-yl)carbamate 
• 1437710-38-7 (S)-6,6-dimethyl-1-phenylhept-4-yn-3-ol 

Relevant academic research and scientific papers

Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines

α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.

Formation of β-Oxo- N-vinylimidates via Intermolecular Ester Incorporation in Huisgen Cyclization/Carbene Cascade Reactions

Unusual intermolecular trapping of esters by carbenes generated via a Huisgen cyclization/retroelectrocyclization/dediazotization cascade reaction is presented. β-Oxo-N-vinylimidates could be obtained in one step from propargyl carbonazidates. Mechanistic control experiments suggested reversible dipole formation by ester addition to the carbene, and nitrogen attack to the ester carbonyl was irreversibly followed by stereoselective decarboxylative elimination to give the Z-vinyl imidate. The cross-conjugated enone, imidate, and enamine functional groups in the β-oxo-N-vinylimidates offer novel syntheses of functionalized oxazoles.

Highly regioselective gold-catalyzed formal hydration of propargylic: Gem -difluorides

Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility of the difluoromethylene unit as a directing group in catalysis.

Enantioselective synthesis and cross-coupling of tertiary propargylic boronic esters using lithiation-borylation of propargylic carbamates

Lithiation-borylation of propargylic carbamates leads to tertiary propargylic boronic esters in very high e.r., provided that ethylene glycol boronic esters are used. These versatile intermediates undergo a range of highly stereoselective transformations, including protodeboronation to give tertiary allenes and Suzuki-Miyaura cross-couplings of tertiary boron species leading to tetrasubstituted allenes with high enantiospecificity. Copyright

Radical cyclization of α-bromo aluminum acetals onto alkenes and alkynes (radic[al] process): A simple access to γ-lactols and 4-methylene-γ-lactols

An efficient preparation of γ-lactols and methylene-γ-lactols is described. Highly acid-sensitive lactols are prepared in a concise manner by using a radical cyclization of aluminum acetals. The precursors for the radical reactions are readily prepared fr

Nickel-catalyzed Negishi cross-couplings of secondary nucleophiles with secondary propargylic electrophiles at room temperature

(Chemical Equation Presented) Mild thing: The first nickel-based catalysts for cross-couplings of secondary organometallic nucleophiles with secondary alkyl electrophiles have been developed. Thus, Negishi reactions proceed under mild conditions (at room temperature with no basic activators) in the presence of NiCl2·glyme and a tridentate ligand (see scheme).

Preparation of propargyl hydroperoxides by regioselective oxidation of allenic zinc reagents with molecular oxygen

Treatment of allenic zinc reagents (R1R2C=C=C(R 3)ZnL), generated by the reaction of propargyl derivative (R 1R2C(X)C≡CH) with triorganozincates (R 33ZnLi), under oxygen atmosphe

Intramolecular iron(II)-catalyzed addition reactions of propargyloxycarbonyl azides

The Fe(II)-catalyzed dediazotation of the propargyl-oxycarbonyl azides 2-4 was studied. In the case of phenyl- (2) and n-butyl-substituted (3) alkynes the products 5 and 6 of an intramolecular syn-aminochlorination were isolated in excellent yields (81-99