A one-pot C-H insertion/olefination sequence for the formation of α-alkylidene-γ-butyrolactones.
A one-pot C-H insertion/olefination sequence for the conversion of α-diazo-α-(dialkoxyphosphoryl)acetates into α-alkylidene-γ-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.
Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
Matthew G
MG
Lloyd
Richard J K
RJ
Taylor
William P
WP
Unsworth
D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D009942:Organometallic Compounds; D012238:Rhodium; D015107:4-Butyrolactone