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Study on enantiomerically pure 2-substituted N,N-dialkyl-1-naphthamides: resolution, absolute stereochemistry, and application to desymmetrization of cyclic meso anhydrides by Wei-Min Dai; Kelly Ka Yim Yeung; Chun Wo Chow; Ian D. Williams is a Chemistry article available to read on EtoBox.

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The axially chiral 2-substituted N,N-diisopropyl-1-naphthamides 1 and 2 were resolved by HPLC over a chiral stationary phase to provide enantiomerically pure atropisomers. The absolute stereochemistry of (-)-syn-1 was determined by X-ray crystallographic analysis of the corresponding (1S)-camphanic acid ester derivative. Desymmetrization of cyclic meso anhydrides 5a and 5b using (-)-syn-1 gave a single diastereomer in good yield.

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Author

Wei-Min Dai; Kelly Ka Yim Yeung; Chun Wo Chow; Ian D. Williams

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2001

Language

EN

Field

Chemistry (Physical Sciences)