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- W1988830994 abstract "The dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as α-methylbenzyl) is stereospecific and retentive not because of a configurationally stable organolithium intermediate but because the starting material exists as two atropisomers at −78°C, of which only one is lithiated. The initially formed ortholithiated amide can be trapped with MeI to give single diastereoisomers of atropisomeric amides bearing chiral N-substituents. Given time, even in the absence of DMPU, the ortholithiated amide undergoes anion translocation to an α-lithiated species, which can cyclise only to one diastereoisomer of the product, leading to the observed stereospecificity." @default.
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- W1988830994 date "1999-11-01" @default.
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- W1988830994 title "Diastereoselective ortholithiation and conformational control in stereospecific dearomatising anionic cyclisations" @default.
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- W1988830994 doi "https://doi.org/10.1016/s0040-4039(99)01766-9" @default.
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