Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold

Authors
Dolle, RE Barden, MC Brennan, PE Ahmed, G Tran, V Ho, DM
Citation
Re. Dolle et al., Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold, TETRAHEDR L, 40(15), 1999, pp. 2907-2908
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
15
Year of publication
1999
Pages
2907 - 2908
Database
ISI
SICI code
0040-4039(19990409)40:15<2907:AOTIAI>2.0.ZU;2-H
Abstract
Hydrazone 4 undergoes tandem intramolecular Michael addition - intramolecul ar azomethine imine cycloaddition in ethanol at reflux to furnish the tricy clic pyrazoline methyl ester 3 in 75% yield. A five-step conversion of 3 to N-1-Alloc-6-(N-Boc-aminomethyl)-1-azaspiro[4.4]nonane-2-acetic acid I prov ides access to a unique tri-functionalized scaffold for combinatorial chemi stry. (C) 1999 Elsevier Science Ltd. All rights reserved.