Pd-catalysed [3 + 3] annelations in the stereoselective synthesis of indolizidines

• Olivier Y. Provoost,
• Andrew J. Hazelwood and
• Joseph P. A. Harrity

Beilstein J. Org. Chem. 2007, 3, No. 8, doi:10.1186/1860-5397-3-8

• , we have turned our attention to the employment of this technique in the synthesis of indolizidines. Specifically, and as outlined in Scheme 1, we envisaged that a key piperidine intermediate 3 could be prepared in enantiomerically pure form and converted into a functionalised indolizidine

• indolizidines (Scheme 5). [3 + 3] Annelation approach to indolizidine skeleta. Enantiospecific aziridine synthesis (ADDP: 1,1'-(azodicarbonyl)dipiperidine). Diastereoselective aldol addition. Indolizidinone formation. Preparation of a functionalised indolizidine. Investigation of the [3 + 3] annelation reaction