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

Autor:	Varlet T; Institut de Chimie des Substances Naturelles, Université Paris-Saclay, ICSN-CNRS UPR, 2301 Gif sur Yvette, France., Matišić M; Institut de Chimie des Substances Naturelles, Université Paris-Saclay, ICSN-CNRS UPR, 2301 Gif sur Yvette, France., Van Elslande E; Institut de Chimie des Substances Naturelles, Université Paris-Saclay, ICSN-CNRS UPR, 2301 Gif sur Yvette, France., Neuville L; Institut de Chimie des Substances Naturelles, Université Paris-Saclay, ICSN-CNRS UPR, 2301 Gif sur Yvette, France., Gandon V; Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO) and Laboratoire de Chimie Moléculaire (LCM), 91405 Orsay, France.; Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, École Polytechnique, Institut Polytechnique de Paris, Route de Saclay, 91128 Palaiseau Cedex, France., Masson G; Institut de Chimie des Substances Naturelles, Université Paris-Saclay, ICSN-CNRS UPR, 2301 Gif sur Yvette, France.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2021 Aug 04; Vol. 143 (30), pp. 11611-11619. Date of Electronic Publication: 2021 Jul 23.
DOI:	10.1021/jacs.1c04648
Abstrakt:	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.
Databáze:	MEDLINE
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