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A One-Pot C-H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones
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| Journal | Organic Letters |
|---|---|
| Date | E-pub ahead of print - 2 May 2014 |
| Date | Published (current) - 2014 |
| Issue number | 10 |
| Volume | 16 |
| Number of pages | 4 |
| Pages (from-to) | 2772-2775 |
| Early online date | 2/05/14 |
| Original language | English |
Abstract
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.
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