Stereospecific Cross-Coupling of α-(Thiocarbamoyl)organostannanes

Significance

The authors present a useful general stereospecific cross-coupling method between pyrrolidinylthiocarbamoyl-protected α-hydroxy­stannanes and alkenyl, aryl, and heteroaryl iodides. The reaction proceeds at mild and neutral conditions and displays a high tolerance towards a variety of functional groups including nitro and keto groups. The configuration at the alkenyl-substituted stereocenters is retained. The configuration of the stannyl-substituted stereocenter is also preserved, although a slight decrease in enantiomeric purity is observed. This loss of chirality can be suppressed by applying lower temperatures at the expense of isolated yields.