Prev. Article Next Article Table of Contents

Letter

Catalytic Diastereoselective Reductive Claisen Rearrangement

Supporting Info

Steven P. Miller and James P. Morken*

Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290

Org. Lett., 2002, 4 (16), pp 2743–2745

DOI: 10.1021/ol026273b

Publication Date (Web): July 13, 2002

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, morken@unc.edu

Abstract

A catalytic amount of [(cod)RhCl]₂ and MeDuPhos initiates an ester enolate Claisen rearrangement with good yields and diastereocontrol. Reaction conditions are mild and tolerant of base-sensitive functionality.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue August 08, 2002
Received May 31, 2002

Recommend & Share

Related Content

Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic ApproachJournal of the American Chemical Society
- Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach
  Jeremy M. Richter, Yoshihiro Ishihara, Takeshi Masuda, Brandon W. Whitefield, Toms Llamas, Antti Pohjakallio and Phil S. Baran
  Journal of the American Chemical Society 2008 130 (52), pp 17938–17954
  Abstract: Full details are provided for the total synthesis of several members of the hapalindole family of natural products, including hapalindole Q, 12-epi-hapalindole D, 12-epi-fischerindole U, 12-epi-fischerindole G, 12-epi-fischerindole I, and welwitindolinone ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Total Synthesis and Structure Elucidation of (+)-Phorbasin CJournal of the American Chemical Society
- Total Synthesis and Structure Elucidation of (+)-Phorbasin C
  Todd K. Macklin and Glenn C. Micalizio
  Journal of the American Chemical Society 2009 131 (4), pp 1392–1393
  Abstract: The first total synthesis and structure elucidation of a member of the phorbasin class of natural products is described.
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane SkeletonJournal of the American Chemical Society
- Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton
  Tanja Gaich and Johann Mulzer
  Journal of the American Chemical Society 2009 131 (2), pp 452–453
  Abstract: Herein we report the first total synthesis of Penifulvin A, a sesquiterpenoid with a novel dioxa-fenestrane structure. Penifulvin A is a potent insecticide against the fall armyworm Spodoptera frugiperda which causes enormous damage in the US by consuming ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Letter

Catalytic Diastereoselective Reductive Claisen Rearrangement

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach

Total Synthesis and Structure Elucidation of (+)-Phorbasin C

Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES