Synthesis of 2,5-disubstituted tetrahydrofurans catalyzed by palladium(0)

Authors
Hara, O Fujii, K Hamada, Y Sakagami, Y
Citation
O. Hara et al., Synthesis of 2,5-disubstituted tetrahydrofurans catalyzed by palladium(0), HETEROCYCLE, 54(1), 2001, pp. 419-424
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
54
Issue
1
Year of publication
2001
Pages
419 - 424
Database
ISI
SICI code
0385-5414(20010101)54:1<419:SO2TCB>2.0.ZU;2-M
Abstract
A stereoselective cyclization of an allylic ester to 2,5-disubstituted tetr ahydrofurans catalyzed by palladium(0) is demonstrated. In this cyclization , acetoxy heptenol (6a) having a free hydroxy group prefered trans isomer t o cis isomer. By the use of the protected acetoxy heptenol (6b), the cis se lectivity was observed. The stereoselectivity was enhanced by the use of DP PIO ligand.