ChemInform Abstract: Stereoselective Synthesis of (Z)-α-Alkylidene-γ- butyrolactone from 2-Alkyn-1-one.

✍ Scribed by F.-T. LUO; M.-W. WANG; Y.-S. LIU

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199717090

✦ Synopsis

Stereoselective Synthesis of (Z)-α-Alkylidene-γ-butyrolactone from 2-Alkyn-1-one. -Reduction of the recently reported (Z)-3-iodo-3-alken-1ones (I) with sodium borohydride gives the corresponding alkenols (II) without loss of stereochemistry. These undergo a Pd(0)-catalyzed cyclization with CO to form the (Z)-alkylidene γ-butyrolactones (IV).