Study on enantiomerically pure 2-substituted N,N-dialkyl-1-naphthamides: resolution, absolute stereochemistry, and application to desymmetrization ofcyclic meso anhydrides

Authors
Dai, WM Yeung, KKY Chow, CW Williams, ID
Citation
Wm. Dai et al., Study on enantiomerically pure 2-substituted N,N-dialkyl-1-naphthamides: resolution, absolute stereochemistry, and application to desymmetrization ofcyclic meso anhydrides, TETRAHEDR-A, 12(11), 2001, pp. 1603-1613
Citations number
79
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
11
Year of publication
2001
Pages
1603 - 1613
Database
ISI
SICI code
0957-4166(20010704)12:11<1603:SOEP2N>2.0.ZU;2-O
Abstract
The axially chiral 2-substituted N,N-diisoproyl-1-1-naphthamides 1 and 2 we re resolved by HPLC over a chiral stationary phase to provide enantiomerica lly pure atropisomers. The absolute stereochemistry of was determined by X- ray crystallographic analysis of the corresponding (1S)-camphanic acid deri vative. Desymmetrization of cyclic meso anhydrides 5a and 5b using (-)-syn- 1 gave a single diastercomer in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.