Developing new reaction methods to assemble densely functionalized heterocyclic cores is critical to increasing the chemical space of accessible pharmacophores. The functionalization of carbon-hydrogen bonds has emerged as a key strategy for producing complicated cores from relatively simple and inexpensive starting materials. We have recently developed a carbon-hydrogen insertion method to synthesize 1,2,3<i>−</i>trisubstituted indolines with excellent control over regio-, diastereo-, and enantioselectivity. The 2-3 carbon-carbon bond of the indoline is assembled by the intramolecular C-H insertion of a rhodium carbenoid into an N-substituted aniline. Broad functional group tolerance, including both free and protected indolines, has been established, indicating that our method can be utilized in the synthesis of complex indoline containing natural products.

Synthesis of indolines by enantioselective C−H insertion reactions of donor-donor metal carbenoids

253rd National Meeting (2017)

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