One-pot three-component syntheses of indoloquinolizidine derivatives using an organocatalytic michael addition and subsequent pictet-spengler cyclization

摘要

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.