Rhodium(I)-catalyzed addition of phenols to dienes. A new convergent synthesis of vitamin E

Authors
Bienayme, H Ancel, JE Meilland, P Simonato, JP
Citation
H. Bienayme et al., Rhodium(I)-catalyzed addition of phenols to dienes. A new convergent synthesis of vitamin E, TETRAHEDR L, 41(18), 2000, pp. 3339-3343
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
18
Year of publication
2000
Pages
3339 - 3343
Database
ISI
SICI code
0040-4039(20000429)41:18<3339:RAOPTD>2.0.ZU;2-R
Abstract
A highly convergent and atom-economical synthesis of (dl)-[alpha]-tocophero l (vitamin E) is proposed, the realization of which was made possible by th e discovery of the regioselective Rh(I)-catalyzed arylation of beta-springe ne with trimethylhydroquinone. Other phenolic compounds and 2-substituted-1 ,3-dienes were shown to undergo this transformation. (C) 2000 Elsevier Scie nce Ltd. All rights reserved.