406215-48-3Relevant articles and documents
The organocatalytic enantioselective [3+2] cycloaddition reaction of α,β-unsaturated aldehydes with azomethine ylides applied to the asymmetric synthesis of densely substituted pyrroloisoquinolines
Iza, Ainara,Ugarriza, Iratxe,Uria, Uxue,Reyes, Efraím,Carrillo, Luisa,Vicario, Jose L.
, p. 8878 - 8884 (2013/09/23)
The synthesis of densely functionalized pyrrolo[2,1-a]isoquinolines was accomplished using the organocatalytic [3+2] cycloaddition between enals and azomethine ylides under iminium catalysis developed in our group some years ago as the key step. The cyclo
Asymmetric synthesis of the protoberberine alkaloid (s)-(-)-xylopinine using enantiopure sulfinimines
Davis, Franklin A.,Mohanty, Pradyumna K.
, p. 1290 - 1296 (2007/10/03)
A concise enantioselective synthesis of (S)-(-)-xylopinine (1) is described involving the addition of the laterally lithiated derivative of o-tolunitrile of 16 to enantiopure sulfinimine (+)-14. Treatment of the resulting cyano sulfinamide adduct (-)-17b with DIBAL-H accomplishes five operations in a single pot and furnishes the cyclic imine (+)-18 in good yield. Reduction and cyclization affords (S)-(-)-1. Alternatively basic hydrolysis of 17b,c gives isoquinolone 21 that is cyclized and reduced to give (S)-(-)-1.