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

Thomas Varlet | Zendy; Mateja Matišić | Zendy; Elsa Van Elslande | Zendy; Luc Neuville | Zendy; Vincent Gandon | Zendy; Géraldine Masson | Zendy

Open Access

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

Author(s) -

Thomas Varlet,

Mateja Matišić,

Elsa Van Elslande,

Luc Neuville,

Vincent Gandon,

Géraldine Masson

Publication year - 2021

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.1c04648

Subject(s) - stereocenter , enantioselective synthesis , chemistry , diastereomer , phosphoric acid , cycloaddition , catalysis , combinatorial chemistry , organocatalysis , stereochemistry , organic chemistry

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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