ChemInform Abstract: Unusual Diastereoselection in the Synthesis of Nine-Membered Ring Lactams and Conformation-Controlled Transannular Reactions to Generate Optically Active Indolizidinones.

Unusual Diastereoselection in the Synthe

Unusual Diastereoselection in the Synthesis of Nine-Membered Ring Lactams and Conformation-Controlled Transannular Reactions to Generate Optically Active Indolizidinones

✍ Alexander Sudau; Udo Nubbemeyer 📂 Article 📅 1998 🏛 John Wiley and Sons 🌐 English ⚖ 131 KB 👁 1 views

The aza-Claisen rearrangement of vinylpyrrolidines 1 yielded almost exclusively the trans-3,8-disubstituted nine-membered ring lactams 2 (TBS=tBuMe Si), independent of whether cis or trans isomers were used as starting materials. The conformation (which provided facial chirality) of the medium-sized