7-Substituted bicyclo[3.2.0]hept-2-en-6-one derivatives were identified as intermediates towards biologically interesting compounds. An improved synthesis of 7-alkyl-7-bromobicyclo[3.2.0]hept-2-en-6-ones by palladium- catalysed [π2a+π2s] cycloaddition of α-bromoalkyl ketenes to cyclopentadiene is described. Increased yields and increasing exo alkyl cycloadducts were observed with various palladium catalysts under standard dehydrochlorination conditions. (C) 2000 Elsevier Science Ltd.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry
- Bicyclic aliphatic compounds