1160851-06-8

Basic information

• Product Name: (2S,3R)-3-(4-fluorophenyl)oxirane-2-carbaldehyde
• Synonyms: (2S,3R)-3-(4-fluorophenyl)oxirane-2-carbaldehyde
• CAS NO: 1160851-06-8
• Molecular Weight: 166.152
• Mol File: 1160851-06-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2S,3R)-3-(4-fluorophenyl)oxirane-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-(4-fluorophenyl)oxirane-2-carbaldehyde(1160851-06-8)
• EPA Substance Registry System: (2S,3R)-3-(4-fluorophenyl)oxirane-2-carbaldehyde(1160851-06-8)

Safety Data

• Hazardous Substances Data: 1160851-06-8(Hazardous Substances Data)

Upstream product

• 51791-26-5 3-(4-fluoro-phenyl)-propenal 
• 24654-55-5 trans-4-fluorocinnamaldehyde 

Relevant articles and documents

Enantiocomplementary Epoxidation Reactions Catalyzed by an Engineered Cofactor-Independent Non-natural Peroxygenase

Peroxygenases are heme-dependent enzymes that use peroxide-borne oxygen to catalyze a wide range of oxyfunctionalization reactions. Herein, we report the engineering of an unusual cofactor-independent peroxygenase based on a promiscuous tautomerase that accepts different hydroperoxides (t-BuOOH and H2O2) to accomplish enantiocomplementary epoxidations of various α,β-unsaturated aldehydes (citral and substituted cinnamaldehydes), providing access to both enantiomers of the corresponding α,β-epoxy-aldehydes. High conversions (up to 98 %), high enantioselectivity (up to 98 % ee), and good product yields (50–80 %) were achieved. The reactions likely proceed via a reactive enzyme-bound iminium ion intermediate, allowing tweaking of the enzyme's activity and selectivity by protein engineering. Our results underscore the potential of catalytic promiscuity for the engineering of new cofactor-independent oxidative enzymes.

ORGANIC SALTS AND METHOD FOR PRODUCING CHIRAL ORGANIC COMPOUNDS

The invention relates to a method for producing chiral organic compounds by asymmetric catalysis, using ionic catalysts comprising a chiral catalyst anion. The claimed method is suitable for reactions which are carried out over cationic intermediate stages, such as iminium ions or acyl pyridinium ions. The invention enables the production of chiral compounds with high ee values, that until now could only be obtained by means of costly purification methods.