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

Authors
Clayden, J Westlund, N Wilson, FX
Citation
J. Clayden et al., Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide, TETRAHEDR L, 40(17), 1999, pp. 3329-3330
Citations number
7
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
17
Year of publication
1999
Pages
3329 - 3330
Database
ISI
SICI code
0040-4039(19990423)40:17<3329:SOA2BS>2.0.ZU;2-3
Abstract
Unlike the corresponding aldehydes, 2-(N-methylformimino)-N,N-dialkyl-1-nap hthamides react highly atroposelectively with simple organolithium reagents to give atropisomeric amines whose syn stereochemistry is thermodynamicall y preferred over anti. (C) 1999 Elsevier Science Ltd. All rights reserved.