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Issue 9, 2017
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Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals

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Abstract

Herein, we describe an efficient method to prepare enantiomerically pure 8-oxabicyclo[3.2.1]octanes via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement of glycal derived 1,6-enyne bearing propargylic carboxylates. The resultant compounds could then undergo interrupted Nazarov cyclization to afford diastereomerically pure 11-oxatricyclo[5.3.1.0]undecanes.

Graphical abstract: Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals

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Publication details

The article was received on 12 Jun 2017, accepted on 31 Jul 2017 and first published on 07 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02625K
Citation: Chem. Sci., 2017,8, 6656-6661
  • Open access: Creative Commons BY license
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    Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals

    H. Liao, W. Leng, K. Le Mai Hoang, H. Yao, J. He, A. Y. H. Voo and X. Liu, Chem. Sci., 2017, 8, 6656
    DOI: 10.1039/C7SC02625K

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