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Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition

Abstract : A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.
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https://hal.archives-ouvertes.fr/hal-03402302
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Submitted on : Monday, October 25, 2021 - 4:11:50 PM
Last modification on : Tuesday, January 4, 2022 - 6:49:41 AM

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Thomas Varlet, Mateja Matišić, Elsa van Elslande, Luc Neuville, Vincent Gandon, et al.. Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition. Journal of the American Chemical Society, American Chemical Society, 2021, 143 (30), pp.11611-11619. ⟨10.1021/jacs.1c04648⟩. ⟨hal-03402302⟩

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