Tandem glycol cleavage - intramolecular 4+2 cycloadditions mediated by Mn(OAc)(3)

Authors
Lena, JIC Ferreira, MDR Hernando, JIM Altinel, E Arseniyadis, S
Citation
Jic. Lena et al., Tandem glycol cleavage - intramolecular 4+2 cycloadditions mediated by Mn(OAc)(3), TETRAHEDR L, 42(18), 2001, pp. 3179-3182
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
18
Year of publication
2001
Pages
3179 - 3182
Database
ISI
SICI code
0040-4039(20010430)42:18<3179:TGC-I4>2.0.ZU;2-#
Abstract
The Mn(OAc)(3) mediated oxidative cleavage of 1 and 2 proceeded as expected , while molecular diversity was generated upon cleavage of their unsaturate d counterparts 5 and 6 via a tandem glycol cleavage/4+2 process. Minor prod ucts of the reaction were identified as the alpha -dicarbonyl derivative (i .e. 25) and the corresponding cross-conjugated hydroxy dienone (i.e. 26). T he process tolerates a variety of substitution patterns and protecting grou ps. A brief comparison with the Pb(OAc), initiated cascade transformations is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.