ChemInform Abstract: Asymmetric Diels—Alder Reaction via Enzymatic Kinetic Resolution Using Ethoxyvinyl Methyl Fumarate.

✍ Scribed by Y. KITA; T. NAKA; M. IMANISHI; S. AKAI; Y. TAKEBE; M. MATSUGI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199840102

✦ Synopsis

Asymmetric Diels-Alder Reaction via Enzymatic Kinetic Resolution Using Ethoxyvinyl Methyl Fumarate.

-Various enzymes are tested in the reaction of alcohol (I) with fumarate (II). Method A is found to give optically active fumarate (R)-(III) and to effect intramolecular Diels-Alder reaction of racemic (III) to afford cycloadducts (IV) and (V). With a view to increasing the enantioselectivity observed for the enzymatic kinetic resolution stage, cf. 72% e.e. for (R)-(III), resolution and cycloaddition are carried out as one-pot reaction. This novel methodology leads to cycloadducts, e.g. (IV) and (VII), with improved enantiomeric excess.

-(KITA, Y.; NAKA, T.;