One‐Pot Three‐Component Syntheses of Indoloquinolizidine Derivatives Using an Organocatalytic Michael Addition and Subsequent Pictet–Spengler Cyclization

Abstract

1 pot, 2 stereocenters, 3 components, 4 bonds: An organocatalyzed one-pot three-component cascade sequence towards highly substituted indoloquinolizidines in moderate to good yields with excellent enantioselectivities was developed (see scheme). The absolute stereochemistry at C2 and C12 b was created by the organocatalyzed conjugate addition of in situ formed indole-tethered β-enaminoesters to α,β-unsaturated aldehydes, and a subsequent acid-promoted intramolecular Pictet–Spengler cyclization.