STEREOSELECTIVE SYNTHESIS OF HIGHLY FUNCTIONALIZED PYRROLIDINES VIA 1,3-DIPOLAR CYCLOADDITION REACTIONS ON A SOLID SUPPORT

Authors
HOLLINSHEAD SP
Citation
Sp. Hollinshead, STEREOSELECTIVE SYNTHESIS OF HIGHLY FUNCTIONALIZED PYRROLIDINES VIA 1,3-DIPOLAR CYCLOADDITION REACTIONS ON A SOLID SUPPORT, Tetrahedron letters, 37(51), 1996, pp. 9157-9160
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
51
Year of publication
1996
Pages
9157 - 9160
Database
ISI
SICI code
0040-4039(1996)37:51<9157:SSOHFP>2.0.ZU;2-U
Abstract
Resin bound 3-hydroxyacetophenone 2 was condensed (NaOMe/MeOH/THF) wit h aryl aldehydes to afford alpha,beta-unsaturated ketones 3a-e. Subseq uent reaction with azomethine ylid 5 in the presence of LiBr/DBU provi ded pyrrolidines 6a-d. These were subsequently acylated and cleaved fr om the solid support to afford highly functionalised pyrrolidines 8a-d . Copyright (C) 1996 Elsevier Science Ltd