89969-01-7

Upstream product

• 26965-15-1 3-phenylhex-5-en-2-one 
• 103-79-7 1-phenyl-acetone 
• 24401-36-3 2-phenyl-4-penten-1-al 
• 82461-23-2 3-phenylhex-5-en-2-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 127-17-3 2-oxo-propionic acid 

Relevant academic research and scientific papers

Bioinspired Radical Stetter Reaction: Radical Umpolung Enabled by Ion-Pair Photocatalysis

A bioinspired, intermolecular radical Stetter reaction of α-keto acids and aldehydes is disclosed that is contingent on a formal “radical umpolung” concept. Enabled by secondary amine activation, electrostatic recognition ensures that the α-ketocarboxylic acids, which function as latent acyl radicals, are proximal to the in situ generated iminium salts. This photoactive contact ion pair is an electron donor–acceptor (EDA) complex, and undergoes facile single electron transfer (SET) and rapid decarboxylation prior to radical–radical recombination. Importantly, decarbonylation is mitigated by this strategy. The initial computational validation on which the process is predicated matches closely with experiment. Synergising organo- and photocatalysis activation principles finally expands the mechanistic and synthetic scope of the classic Stetter reaction to include α,β-unsaturated aldehydes as acceptors.

Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones including whisky and cognac lactones and crobarbatic acid

Oxidation of 2-alkoxy-3,4-dihydro-2H-pyrans 3 with dimethyldioxirane or MTO/urea-H2O2 followed by Jones oxidation leads to rearrangement and stereocontrolled formation of 4,5-cis-disubstituted tetrahydrofuranones. The method is applied to the synthesis of the whisky lactone 9, cognac lactone 10 and crobarbatic acid 17.

Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones

Lewis acids are employed as catalysts in the annulation of 1,4- and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) end ethers of β-diketones and β-keto esters. A variety of 2-(alkoxycarbonyl)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regiocontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation reaction.

ELECTROPHILE-INITIATED CONVERSION OF A PROSTAGLANDIN ENDOPEROXIDE MODEL COMPOUND TO THE THROMBOXANE B SKELETON

Reaction of the simplified prostaglandin endoperoxide model (1) with ferric or cupric ion afforded the lactols (2a, b) containing the thromboxane B ring moiety, along with ketol (3) and levulinaldehyde derivatives (4, 5).