6533b85afe1ef96bd12b89c0
RESEARCH PRODUCT
ChemInform Abstract: First Synthesis of Medium-Sized Ring Allenyl Lactams.
Dieter SchollmeyerMoritz PerscheidUdo Nubbemeyersubject
Claisen rearrangementchemistry.chemical_compoundOlefin fiberchemistryStereochemistryAlleneGeneral MedicineRing (chemistry)Unit (ring theory)description
Medium-sized lactams bearing an axially chiral allene unit have been synthesized by using an aza-ketene Claisen rearrangement. Starting from 2-alkynylpiperidines or 2-alkynylazepines, ring enlargement enabled the highly diastereoselective formation of 10- or 11-membered lactams with a 4,5-allene subunit. X-ray analysis of the allenylacezinone showed the presence of a strained cumulated olefin system with a defined arrangement of the functional groups. The cyclic allenes were found to be stable upon heating up to 50 °C.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-01-23 | ChemInform |