Organocatalytic Asymmetric Synthesis of <i>α</i>‐Trifluoromethyl Homoallylic Amine Derivatives from Trifluoromethyl‐Containing Ketoimines and Isatin‐Derived Morita‐Baylis‐Hillman Carbonates

Abstract

Abstract The asymmetric γ ‐regioselective‐alkylation reaction which is catalyzed by a chiral tertiary amine ((DHQ) 2 PHAL) and takes advantage of isatin‐derived Morita‐Baylis‐Hillman carbonates and CF 3 ‐contained ketoimines, delivered chiral α ‐trifluoromethylamine derivatives and incorporated an oxindole motif in yields of 65–98%, diastereoselectivities (&gt;20:1 in most cases) and enantioselectivities of 73–99%. The subsequent deprotection gave α ‐ trifluoromethyl amines in a stereoselective manner. Furthermore, fused polycyclic frameworks can be furnished by subsequent derivatization of the product without eroding its stereoselectivity. magnified image

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