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Highly Diastereoselective Synthesis of Fully Substituted Tetrahydrofurans by a One-Pot Cascade Reaction of Aryldiazoacetates with Allyl Alcohols

  1. Xinfang Xu1,
  2. Xingchun Han1,2,
  3. Liping Yang Prof.1,
  4. Wenhao Hu Prof.1,3

Article first published online: 28 OCT 2009

DOI: 10.1002/chem.200902093

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 15, Issue 46, pages 12604–12607, November 23, 2009

Additional Information

How to Cite

Xu, X., Han, X., Yang, L. and Hu, W. (2009), Highly Diastereoselective Synthesis of Fully Substituted Tetrahydrofurans by a One-Pot Cascade Reaction of Aryldiazoacetates with Allyl Alcohols. Chemistry - A European Journal, 15: 12604–12607. doi: 10.1002/chem.200902093

Author Information

  1. 1

    Department of Chemistry, East China Normal University, Shanghai, 200062 (China), Fax: (+86) 021-62233176

  2. 2

    Roche R&D Center (China) Ltd. Shanghai, 201203 (China)

  3. 3

    State Key Laboratory and Institute of Elemento-organic Chemistry, Nakai University, Tianjin 300071 (China)

Publication History

  1. Issue published online: 18 NOV 2009
  2. Article first published online: 28 OCT 2009
  3. Manuscript Received: 28 JUL 2009

Funded by

  • National Science Foundation of China. Grant Number: 20872036
  • Shanghai Municipal Education Commission. Grant Number: 09ZZ45
  • Science and Technology Commission of Shanghai Municipality. Grant Number: 09JC1404900

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Keywords:

  • diastereoselectivity;
  • domino reactions;
  • Michael addition;
  • O[BOND]H insertion;
  • tetrahydrofurans

Graphical Abstract

Thumbnail image of graphical abstract

A cascade of tetrahydrofurans: A one-pot cascade reaction for the preparation of fully substituted tetrahydrofurans from aryldiazoacetates and allyl alcohols is reported. Rh-catalyzed diazo decomposition of diazoacetates 1 with a secondary alcohols 2 gave an O[BOND]H insertion product with excellent diastereoselectivity. Subsequent intramolecular Michael-type addition produced the desired tetrahydrofurans 3 with excellent stereoselective control.

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