Asymmetric syntheses of 8-oxabicyclo[3, 2, 1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals. Issue 9 (7th August 2017)

• Record Type: Journal Article
• Authors: Liao, Hongze; Leng, Wei-Lin; Le Mai Hoang, Kim; Yao, Hui; He, Jingxi; Voo, Amanda Ying Hui; Liu, Xue-Wei
• Is Part Of: Chemical science. Volume 8:Issue 9(2017)
• Page Start: 6656
• Page End: 6661
• Publication Date: 2017-08-07
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc02625k
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A gold-catalyzed tandem 1, 3-acyloxy migration/Ferrier rearrangement to access 8-oxabicyclo[3.2.1]octanes with high efficiency and complete diastereoselectivity was developed successfully. Resultant compounds could undergo the interrupted Nazarov cyclization to afford diastereomerically pure 11-oxatricyclo[5.3.1.0]undecanes. 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.