A short stereoselective synthesis of (+)- and (−)-2-oxabicyclo[3.3.0]oct-6-en-3-one by intramolecular carbon–hydrogen insertion catalyzed by chiral dirhodium(II) carboxamidates

✍ Scribed by Michael P Doyle; Arthur J Catino

• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 114 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00083-1

✦ Synopsis

The synthesis of (1S,5R)-(-)-2-oxabicyclo[3.3.0]oct-6-en-3-one, a useful synthetic precursor en route to various prostaglandins, from divinylcarbinol via catalytic metathesis and C H insertion of 3-cyclopentenyl diazoacetate is described. Enantioselectivities of 90±1% have been achieved in the insertion process.