Prev. Article Next Article Table of Contents

Letter

Pd(0)-Catalyzed Coupling−Cyclization of 2-(2‘,3‘-Allenyl)acetylacetates and Organic Halides: An Efficient Synthesis of 4,5-Dihydrofuran Derivatives

Supporting Info

Shengming Ma,* Zilong Zheng, and Xuefeng Jiang

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China

Org. Lett., 2007, 9 (3), pp 529–531

DOI: 10.1021/ol0628917

Publication Date (Web): January 13, 2007

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

, masm@mail.sioc.ac.cn

Abstract

Highly chemo- and regioselective Pd(0)-catalyzed coupling−cyclization of 2-(2‘,3‘-allenyl)acetylacetates with organic halides using K₃PO₄ as base in DMF efficiently afforded 4,5-dihydrofuran derivatives in moderate to excellent yields, with a selectivity of >97:3.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue February 01, 2007
Received November 29, 2006

Recommend & Share

Related Content

Pd-Catalyzed Regio- and Stereoselective Cyclization−Heck Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids with AlkenesOrganic Letters
- Pd-Catalyzed Regio- and Stereoselective Cyclization−Heck Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids with Alkenes
  Fei Yu, Xiongdong Lian, and Shengming Ma
  Organic Letters 2007 9 (9), pp 1703–1706
  Abstract: The cyclization−Heck reactions of monoesters of 1, 2-allenyl phosphonic acids with alkenes were studied. The reaction afforded 4-(1-Z-alkenyl)-2-ethoxy-2,5-dihydro[1,2]oxaphosphole 2-oxides regio- and stereoselectively. Pd(II) was regenerated from the in ...
  Abstract | Full Text HTML | Hi-Res PDF
Observation of New Cycloisomerization Pattern of 1,5-Bisallenes. Catalyst and Substituent EffectsOrganic Letters
- Observation of New Cycloisomerization Pattern of 1,5-Bisallenes. Catalyst and Substituent Effects
  Ping Lu and Shengming Ma
  Organic Letters 2007 9 (11), pp 2095–2097
  Abstract: In this paper a new cycloisomerization pattern of 1,5-bisallenes based on the catalyst and substituent effects has been reported. A range of seven-membered cross-conjugated trienes 7 would be obtained efficiently via the β-H elimination and reductive ...
  Abstract | Full Text HTML | Hi-Res PDF
Rh-Catalyzed Triple Allene Approach to Bicyclo[4.4.0]decene Derivatives and Its Application for the Stepwise Synthesis of Steroid-Like Tetracyclic SkeletonsOrganic Letters
- Rh-Catalyzed Triple Allene Approach to Bicyclo[4.4.0]decene Derivatives and Its Application for the Stepwise Synthesis of Steroid-Like Tetracyclic Skeletons
  Ping Lu and Shengming Ma
  Organic Letters 2007 9 (25), pp 5319–5321
  Abstract: The construction of a new type of bicyclo[4.4.0]decene products with a conjugated exocyclic diene unit was developed using Rh-catalyzed cyclization of 1,5-bisallenes in the presence of monoallenes. The steroid-like tetracyclic products could be obtained ...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Pd(0)-Catalyzed Coupling−Cyclization of 2-(2‘,3‘-Allenyl)acetylacetates and Organic Halides: An Efficient Synthesis of 4,5-Dihydrofuran Derivatives

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Pd-Catalyzed Regio- and Stereoselective Cyclization−Heck Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids with Alkenes

Observation of New Cycloisomerization Pattern of 1,5-Bisallenes. Catalyst and Substituent Effects

Rh-Catalyzed Triple Allene Approach to Bicyclo[4.4.0]decene Derivatives and Its Application for the Stepwise Synthesis of Steroid-Like Tetracyclic Skeletons

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES