Prev. Article Next Article Table of Contents

Communication

Rhodium(I)-Catalyzed [2+2+1] Cycloadditions of 1,3-Dienes, Alkenes, and CO

Supporting Info

Paul A. Wender,* Mitchell P. Croatt, and Nicole M. Deschamps

Department of Chemistry, Stanford University, Stanford, California 94305

J. Am. Chem. Soc., 2004, 126 (19), pp 5948–5949

DOI: 10.1021/ja0489487

Publication Date (Web): April 21, 2004

Abstract

Initial examples of a Rh(I)-catalyzed [2+2+1] reaction of diene-enes and CO are described. This method allows for the facile, efficient, and diastereoselective construction of a variety of alkenyl cyclopentanones in good to excellent yields. Control studies show that the diene moiety is required for this process as bis-enes do not give the [2+2+1] products under the same conditions.

View: Full Text HTML | Hi-Res PDF

Available Supporting Information for This Article

PDF

ja0489487si20040326_102409.pdf (249 KB)

Electronic Supporting Information files are available without a subscription to ACS Web Editions. All files are copyrighted by the American Chemical Society. Files may be downloaded for personal use only. Users are not permitted to reproduce, republish, redistribute, or resell any Supporting Information, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce this material, requesters must process their own requests via the Rightslink permission system. Information about how to use the Rightslink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html. Please read only the part about Rightslink.

Tools

SciFinder Links

Explore by:

Author of this Article Any Author Research Topic

History

Published In Issue May 19, 2004
Received February 24, 2004

Recommend & Share

Related Content

Total Synthesis of VinigrolJournal of the American Chemical Society
- Total Synthesis of Vinigrol
  Thomas J. Maimone, Jun Shi, Shinji Ashida and Phil S. Baran
  Journal of the American Chemical Society 2009 131 (47), pp 17066–17067
  Abstract: The longstanding challenge posed by the complex diterpene vinigrol has been answered for the first time. The notorious difficulty in synthesizing vinigrol stems from its unprecedented decahydro-1,5-butanonaphthalene ring system, eight contiguous ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Total Synthesis of (−)-Nakadomarin AJournal of the American Chemical Society
- Total Synthesis of (−)-Nakadomarin A
  Pavol Jakubec, Dane M. Cockfield and Darren J. Dixon
  Journal of the American Chemical Society 2009 131 (46), pp 16632–16633
  Abstract: A short and highly stereoselective synthesis of (−)-nakadomarin A has been developed using combinations of catalyst-controlled bond formations, one-pot multistep procedures, and powerful route-shortening reaction cascades. Several unprecedented chemical ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Asymmetric Catalysis of the [5 + 2] Cycloaddition Reaction of Vinylcyclopropanes and π-SystemsJournal of the American Chemical Society
- Asymmetric Catalysis of the [5 + 2] Cycloaddition Reaction of Vinylcyclopropanes and π-Systems
  Paul A. Wender, Lars O. Haustedt, Jaehong Lim, Jennifer A. Love, Travis J. Williams, and Joo-Yong Yoon
  Journal of the American Chemical Society 2006 128 (19), pp 6302–6303
  Abstract: As part of our studies of metal-catalyzed [m + n (+...o)] cycloadditions, we have previously reported the rhodium-catalyzed [5 + 2] cycloaddition of vinylcyclopropanes (VCPs) and π-systems. These studies have led to Rh(I) complexes that catalyze these ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Communication

Rhodium(I)-Catalyzed [2+2+1] Cycloadditions of 1,3-Dienes, Alkenes, and CO

Abstract

Available Supporting Information for This Article

PDF

Tools

SciFinder Links

History

Recommend & Share

Related Content

Total Synthesis of Vinigrol

Total Synthesis of (−)-Nakadomarin A

Asymmetric Catalysis of the [5 + 2] Cycloaddition Reaction of Vinylcyclopropanes and π-Systems

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES