Asymmetric deprotonation of N,N-dihexyl-1-naphthamides to provide atropisomers of N,N-dihexyl-2-alkyl-1-naphthamides

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2899-2902

  Thayumanavan, S ^a   Beak, Peter ^a   Curran, Dennis P ^b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHAMIDE DERIVATIVE; AMIDE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029935516     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00439-X     Document Type: Article

References (36)

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16. 10
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30. 11a
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32. The provisional assignments of different absolute configurations assume that the dicyclohexyl and the di-n-hexyl isomers behave in analogous fashion on chromatography.
33. These products were identified by GC-mass spectrometry.
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36. An alternative possibility is that substrate 2 is resolved by the selective addition of butyllithium to the naphthalene nucleus of the (S)-enantiomer of 2. Deprotonation of this resolved atropomer of 2 followed by trapping with methyl iodide could provide (R)-5. This would require 1 and 2 to follow different pathways for enantioselective substitution, since in the former case, there was little addition.