Highly Enantioselective Construction of Multifunctional Silicon‐Stereogenic Silacycles by Asymmetric Enamine Catalysis

Abstract

We report the first highly enantioselective construction of silicon‐stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular aldolization of prochiral siladials was thus developed for the facile access of multifunctional silicon‐stereogenic silacycles in high to excellent enantioselectivity. With an enal moiety, these adducts could be readily elaborated for the diverse synthesis of silicon‐stereogenic compounds, and for late‐stage modification.

The rapid construction and biological evaluation of densely substituted pyrrolo[1,2-a]indoles via a BF3·OEt2-assisted cascade approach

“…1,2 The broad spectrum of biological activity exhibited by indole derivatives renders their synthesis a subject of considerable interest in chemistry and medicine. [3][4][5][6][7][8] The promising applications of cascade reactions to access a variety of natural product scaffolds make them one of the leading and fascinating strategies towards development in organic synthesis. [9][10][11][12] Encouraged by the advancement of cascade reactions, we targeted pyrrolo [1,2-a]indoles possessing a unique 6-5-5 tricyclic ring skeleton.…”

Pseudo-Diastereodivergent Synthesis of Chiral Fluorenes Bearing Bis-1,3-Nonadjacent Stereogenic Centers via Organocatalytic Desymmetrization of meso-Epoxides

“…We also demonstrated that the C/Si switch is feasible for the syn thesis of chiral sila-fluorenes. However, remarkably lower enantioselectivity was observed, probably due to a detrimental longer C–Si bond for chiral induction ( 3r – 3s ) …”