Rearrangement of epoxides in non-aldol aldol process: Allylic vs. tertiaryand secondary carbocationic centers

Authors
Jung, ME Marquez, R
Citation
Me. Jung et R. Marquez, Rearrangement of epoxides in non-aldol aldol process: Allylic vs. tertiaryand secondary carbocationic centers, TETRAHEDR L, 40(16), 1999, pp. 3129-3132
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
16
Year of publication
1999
Pages
3129 - 3132
Database
ISI
SICI code
0040-4039(19990416)40:16<3129:ROEINA>2.0.ZU;2-S
Abstract
It has been shown that allylic carbocations are formed in preference to ter tiary or secondary carbocations in the rearrangement of substituted epoxide s. However protection of the alkene as a bromo ether allows for the desired rearrangement and production of intermediates for the synthesis of the cyt otoxic tedanolides. (C) 1999 Elsevier Science Ltd. All rights reserved.