TY - JOUR
T1 - Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy
AU - Hulme, Christopher
AU - Ma, Liang
AU - Cherrier, Marie Pierre
AU - Romano, Joseph J.
AU - Morton, George
AU - Duquenne, Celine
AU - Salvino, Joseph
AU - Labaudiniere, Richard
PY - 2000/3/18
Y1 - 2000/3/18
N2 - This communication reveals a novel application of the so-called convertible isonitriles for the solution/solid phase generation of γ-lactam analogues. Use of tethered N-BOC aldehydes in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3-step, 1-pot procedure') affords γ-lactams in good yield. The UDC (Ugi/De-BOC/Cyclize) strategy, coupled with a convertible isonitrile, is now feasible from all three substitution sites of the Ugi product. A conceptually novel approach, combining a bi-functional precursor with a post-condensation modification to give fused lactam-ketopiperazines, is also revealed.
AB - This communication reveals a novel application of the so-called convertible isonitriles for the solution/solid phase generation of γ-lactam analogues. Use of tethered N-BOC aldehydes in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3-step, 1-pot procedure') affords γ-lactams in good yield. The UDC (Ugi/De-BOC/Cyclize) strategy, coupled with a convertible isonitrile, is now feasible from all three substitution sites of the Ugi product. A conceptually novel approach, combining a bi-functional precursor with a post-condensation modification to give fused lactam-ketopiperazines, is also revealed.
UR - https://www.scopus.com/pages/publications/0034681853
UR - https://www.scopus.com/pages/publications/0034681853#tab=citedBy
U2 - 10.1016/S0040-4039(00)00052-6
DO - 10.1016/S0040-4039(00)00052-6
M3 - Article
AN - SCOPUS:0034681853
SN - 0040-4039
VL - 41
SP - 1883
EP - 1887
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 12
ER -