AI Article Synopsis
- A new method for synthesizing chiral spirocyclohexyl-indolenines has been developed, allowing for the creation of two different diastereoisomers with high enantioselectivity through a specific catalytic reaction.
- By adjusting the reaction conditions, researchers can efficiently manipulate functional groups to produce enantioenriched spirocyclohexyl-indolines and -oxindoles.
- The underlying reasons for this effective stereocontrol were explored using DFT calculations, suggesting a different mechanism than previous studies involving enecarbamates.
Article 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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| http://dx.doi.org/10.1021/jacs.1c04648 | DOI Listing |
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