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Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide

โœ Scribed by Jonathan Clayden; Neil Westlund; Francis X. Wilson

Book ID
104261303
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
158 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Unlike the corresponding aldehydes, 2-(N-methylformimino)~NJ-dialkyl-I-naphthamides react highly atroposelectively with simple organolithium reagents lo give atropisomeric amines whose svrt stereochemistry is thermodynamically preferred over anti. 0 1999 Elsevier Science Ltd. All rights reserved, Aromatic tertiary amides flanked by two orrho substituents are usually atropisomeric (axially chiral) because of slow rotation about the Ar-CO bond.' Rotationally restricted tertiary amide substituents can be powerful agents for stereocontrol, particularly in lithiated amides,' even at relatively remote centres.4,5 Nucleophilic additions to 2-acyl-1-naphthamides are in general less stereoselective.'j We attributed the poor, metal-dependent stereoselectivity of the additions to 2-formyl-1-naphthamides

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