A Novel 1,2-Migration of Acyloxy, Phosphatyloxy, and Sulfonyloxy Groups in Allenes: Efficient Synthesis of Tri- and Tetrasubstituted Furans

Heading south: The 1,2‐migration of the acyloxy, phosphatyloxy, and sulfonyloxy groups in allenyl systems has been discovered. This migration, combined with the transition‐metal‐catalyzed cycloisomerization reaction, leads to the efficient synthesis of tri‐ and tetrasubstituted acyl‐, phosphatyl‐, a...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 43; no. 17; pp. 2280 - 2282
Main Authors Sromek, Anna W., Kel'in, Alexander V., Gevorgyan, Vladimir
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 19.04.2004
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
cyclization
furans
homogeneous catalysis
Physical Sciences
rearrangement
Science & Technology
synthetic methods
ROUTE
1,2-ACYLOXY MIGRATION
1,2-DIENYL
MECHANISM
CONVERSION
PROPARGYL ESTERS
cyclization
KETONES
homogeneous catalysis
furans
CYCLOISOMERIZATION
rearrangement
synthetic methods
Online AccessGet full text

Cover

More Information
Summary:Heading south: The 1,2‐migration of the acyloxy, phosphatyloxy, and sulfonyloxy groups in allenyl systems has been discovered. This migration, combined with the transition‐metal‐catalyzed cycloisomerization reaction, leads to the efficient synthesis of tri‐ and tetrasubstituted acyl‐, phosphatyl‐, and sulfonyloxy‐substituted furans as single regioisomers.
Bibliography:istex:580F320BBC466FD74F14EF2098B072DFA24EE9AA
We are grateful to the NIH (GM 64444) for financial support of this work. We also thank D. Yap for technical assistance.
ark:/67375/WNG-VMBV2BPV-M
ArticleID:ANIE200353535
Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353535