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 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 cy...
| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2017
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/86867 http://hdl.handle.net/10220/44230 |
| _version_ | 1811681061869977600 |
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| author | Liao, Hongze Leng, Wei-Lin Hoang, Kim Le Mai Yao, Hui He, Jingxi Voo, Amanda Ying Hui Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Liao, Hongze Leng, Wei-Lin Hoang, Kim Le Mai Yao, Hui He, Jingxi Voo, Amanda Ying Hui Liu, Xue-Wei |
| author_sort | Liao, Hongze |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T03:34:58Z |
| format | Journal Article |
| id | ntu-10356/86867 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:34:58Z |
| publishDate | 2017 |
| record_format | dspace |
| spelling | ntu-10356/868672023-02-28T19:34:21Z Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals Liao, Hongze Leng, Wei-Lin Hoang, Kim Le Mai Yao, Hui He, Jingxi Voo, Amanda Ying Hui Liu, Xue-Wei School of Physical and Mathematical Sciences Asymmetric Synthesis Glycals 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. MOE (Min. of Education, S’pore) Published version 2017-12-29T01:43:12Z 2019-12-06T16:30:34Z 2017-12-29T01:43:12Z 2019-12-06T16:30:34Z 2017 Journal Article Liao, H., Leng, W.-L., Hoang, K. L. M., Yao, H., He, J., Voo, A. Y. H., et al. (2017). Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals. Chemical Science, 8(9), 6656-6661. 2041-6520 https://hdl.handle.net/10356/86867 http://hdl.handle.net/10220/44230 10.1039/C7SC02625K en Chemical Science © 2017 The Author(s) (published by Royal Society of Chemistry). This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. 6 p. application/pdf |
| spellingShingle | Asymmetric Synthesis Glycals Liao, Hongze Leng, Wei-Lin Hoang, Kim Le Mai Yao, Hui He, Jingxi Voo, Amanda Ying Hui Liu, Xue-Wei Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals |
| title | Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals |
| title_full | Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals |
| title_fullStr | Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals |
| title_full_unstemmed | Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals |
| title_short | Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals |
| title_sort | asymmetric syntheses of 8 oxabicyclo 3 2 1 octane and 11 oxatricyclo 5 3 1 0 undecane from glycals |
| topic | Asymmetric Synthesis Glycals |
| url | https://hdl.handle.net/10356/86867 http://hdl.handle.net/10220/44230 |
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