A convenient access to (3S)-3-(triisopropylsilyl)oxy-1-pyrrolin N-oxide, auseful intermediate for polyfunctionalized enantiopure indolizidine and pyrrolizidine synthesis

Authors
Goti, A Cacciarini, M Cardona, F Brandi, A
Citation
A. Goti et al., A convenient access to (3S)-3-(triisopropylsilyl)oxy-1-pyrrolin N-oxide, auseful intermediate for polyfunctionalized enantiopure indolizidine and pyrrolizidine synthesis, TETRAHEDR L, 40(14), 1999, pp. 2853-2856
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
14
Year of publication
1999
Pages
2853 - 2856
Database
ISI
SICI code
0040-4039(19990402)40:14<2853:ACAT(N>2.0.ZU;2-C
Abstract
Optimization of a strategy providing the enantiomerically pure nitrone 2 in five steps and 28% overall yield from L-malic acid has been achieved by th e combined use of DIBAL-H as the reductant and triisopropylsilyl as the pro tecting group. The utility of nitrone 2 as synthetic intermediate is demons trated by a ready access to polyhydroxylated indolizidines and pyrrolizidin es via stereoselective 1,3-dipolar cycloaddition reactions. (C) 1999 Elsevi er Science Ltd. All rights reserved.