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

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

Herein, we describe an efficient method to prepare enantiomerically pure 8-oxabicyclo[3.2.1]octanes 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 cycliz...

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Veröffentlicht in:Chemical science (Cambridge) 2017-09, Vol.8 (9), p.6656-6661
Hauptverfasser: Liao, Hongze, Leng, Wei-Lin, Le Mai Hoang, Kim, Yao, Hui, He, Jingxi, Voo, Amanda Ying Hui, Liu, Xue-Wei
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, we describe an efficient method to prepare enantiomerically pure 8-oxabicyclo[3.2.1]octanes 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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc02625k