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4-Substitued azaindolines, which are isosteres of indolines, are useful synthetic building blocks that reduce the risk of bioactivation induced idiosyncratic toxicity have been prepared. Multigram routes to 2,3-dihydro-1H-pyrrolo[2,3-c]pyridine-4-triflate 16, 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile 20 and 4-chloro-2,3-dihydro-1H-pyrrolo[2,3-d]pyridazine 30 are outlined.
Substitution of a t-butyl group at C-6 of the THP ring results in a chiral auxiliary that exerts exceptional stereocontrol in radical addition reactions. For example, radical 2c adds to 2-nitropropene at −78 °C to give, after reductive hydrolysis, the protected aldol 4c with a diastereoselectivity of 35 1. Good selectivity (ds = 8 1) is even observed when the reaction is conducted at ambient temperature...
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