A Central-to-Axial Chirality Conversion Strategy for the Synthesis of C-N Axially Chiral N -Arylpyrroles.

We present a central-to-axial chirality conversion strategy for the construction of C-N axially chiral N -arylpyrroles via a gold(I)-catalyzed 5-endo-dig cyclization/dehydration cascade from amino acid derivatives. The reaction exhibits high efficiency on the central-to-axial chirality conversion. Density functional theory calculations suggest that the stereospecificity during the central-to-axial chirality conversion lies in the stability of the conformations of the amino alcohol and the corresponding low barrier transition state.