Radical cyclization on solid support: Synthesis of gamma-butyrolactones

Authors
Watanabe, Y Ishikawa, S Takao, G Toru, T
Citation
Y. Watanabe et al., Radical cyclization on solid support: Synthesis of gamma-butyrolactones, TETRAHEDR L, 40(17), 1999, pp. 3411-3414
Citations number
29
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
3411 - 3414
Database
ISI
SICI code
0040-4039(19990423)40:17<3411:RCOSSS>2.0.ZU;2-F
Abstract
Synthesis of gamma-butyrolactones using radical cyclization on solid-phase has been achieved. Polymer-supported beta-bromoethylacetals were treated wi th tributyltin hydride in the presence of a catalytic amount of alpha,alpha '-azobisisobutyronitrile to generate intermediate carbon radicals which cyc lize onto the intramolecular carbon-carbon double bond. The cyclization pro ducts were released by Jones oxidation from resin to give gamma-butyrolacto nes in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.