Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis

• Roger Hunter,
• Sophie C. M. Rees-Jones and
• Hong Su

Beilstein J. Org. Chem. 2007, 3, No. 38, doi:10.1186/1860-5397-3-38

• plays a coordinating role in the extended Mukaiyama aldol addition resulting in an endo-like transition state.[11] In the known cases [3][18] of N-alkyl silyloxypyrroles successfully reacting with simple aldehydes just mentioned, a more hindered α-asymmetric benzyl centre on nitrogen was used which

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

• compares well with a close analogue reported by Knapp and co-workers suggesting that the aldol addition reaction proceeds under Felkin-Anh control [see Supporting Information File 1]). In conclusion, we have shown that functionalised indolizidinone intermediates can be generated through the Pd-catalysed [3

• 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