A MECHANISTICALLY UNUSUAL BASE-INDUCED [1,3]-H-SHIFT IN HOMOALLYLIC ETHERS

Authors
MULZER J WILLE G BILOW J ARIGONI D MARTINONI B ROTEN K
Citation
J. Mulzer et al., A MECHANISTICALLY UNUSUAL BASE-INDUCED [1,3]-H-SHIFT IN HOMOALLYLIC ETHERS, Tetrahedron letters, 38(31), 1997, pp. 5469-5472
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
31
Year of publication
1997
Pages
5469 - 5472
Database
ISI
SICI code
0040-4039(1997)38:31<5469:AMUB[I>2.0.ZU;2-5
Abstract
Upon treatment with NaH in DMF the homoallylic ethers 1a-g and the ami ne 1h undergo a rearrangement into the trisubstituted (Epsilon)- olefi ns 2a-h. Experiments with isotopically labelled forms of 1a and 1b sho w that the [1,3]-shift is cleanly intramolecular and proceeds predomin antly in the suprafacial mode. (C) 1997 Elsevier Science Ltd.