Rhodium(III)-catalyzed arylation and alkenylation of imines by C-H functionalizat

Yale University, New Haven CT

Investigators

Abstract

The utilization of transition metal complexes as catalysts for the formation of C-C bonds has emerged as a widely exploited synthetic strategy, both in the construction of pharmaceutical agents and small molecule natural products. However, a common prerequisite is that the molecular components are prefunctionalized, thus leading to wasteful byproducts and additional synthetic sequences. Recently, transition metals such as rhodium have found application in directed C-H functionalization reactions. These reactions make unnecessary the prior functionalization of the molecule, thus streamlining syntheses and decreasing chemical waste. With these considerations in mind, this proposal aims to study three aspects of the Rh(III)-catalyzed arylation of imines recently developed in the Ellman laboratory. This research project will encompass the (1) exploration of directing groups that would serve as versatile synthons in organic synthesis, (2) construction of complex ring systems via C-H functionalization, and (3) development of an asymmetric approach to the Rh(III) C-H functionalization using both a chiral auxiliary and a chiral counterion strategy. These studies will culminate in the synthesis of a number of enantioenriched ?-amino acid and isoindolinone derivatives.