Spiro-cyclopropyl oxindoles are widely found in natural products and medicinal molecules.Herein,we report a highly stereo-and enantio–selective procedure for accessing this class of compounds via tertiary amine media...Spiro-cyclopropyl oxindoles are widely found in natural products and medicinal molecules.Herein,we report a highly stereo-and enantio–selective procedure for accessing this class of compounds via tertiary amine mediated cyclopropanation of ammonium ylides with the in-situ Heck reaction-generated 3-alkenyl indolones as the Michael receptors.This reaction features mild conditions,excellent enantioselectivity(up to 98%)and diastereoselectivity(up to 99:1),high atom-and step-economy,broad substrate scopes,and good functional group tolerance.Additionally,this scalable synthetic process could offer a novel strategy for the efficient synthesis of enantiopure spirocyclopropyl oxindoles.展开更多
文摘Spiro-cyclopropyl oxindoles are widely found in natural products and medicinal molecules.Herein,we report a highly stereo-and enantio–selective procedure for accessing this class of compounds via tertiary amine mediated cyclopropanation of ammonium ylides with the in-situ Heck reaction-generated 3-alkenyl indolones as the Michael receptors.This reaction features mild conditions,excellent enantioselectivity(up to 98%)and diastereoselectivity(up to 99:1),high atom-and step-economy,broad substrate scopes,and good functional group tolerance.Additionally,this scalable synthetic process could offer a novel strategy for the efficient synthesis of enantiopure spirocyclopropyl oxindoles.
