Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile
A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as va...
| Main Authors: | , , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/145625 |
| _version_ | 1826118581770780672 |
|---|---|
| author | Ding, Wei Chai, Jinkui Wang, Chen Wu, Junliang Yoshikai, Naohiko |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Ding, Wei Chai, Jinkui Wang, Chen Wu, Junliang Yoshikai, Naohiko |
| author_sort | Ding, Wei |
| collection | NTU |
| description | A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means. |
| first_indexed | 2024-10-01T04:45:50Z |
| format | Journal Article |
| id | ntu-10356/145625 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:45:50Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1456252023-02-28T19:53:58Z Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile Ding, Wei Chai, Jinkui Wang, Chen Wu, Junliang Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Ethers Hydrocarbons A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means. Ministry of Education (MOE) Accepted version This work was supported by the Ministry of Education(Singapore) and Nanyang Technological University(MOE2016-T2-2-043 and RG114/18). We thank Dr. Yongxin Li (Nanyang Technological University) for his assistance withthe X-ray crystallographic analysis. 2020-12-30T05:03:09Z 2020-12-30T05:03:09Z 2020 Journal Article Ding, W., Chai, J., Wang, C., Wu, J., & Yoshikai, N. (2020). Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile. Journal of the American Chemical Society, 142(19), 8619–8624. doi:10.1021/jacs.0c04140 0002-7863 https://hdl.handle.net/10356/145625 10.1021/jacs.0c04140 32362119 19 142 8619 8624 en Journal of the American Chemical Society This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.0c04140 application/pdf |
| spellingShingle | Science::Chemistry Ethers Hydrocarbons Ding, Wei Chai, Jinkui Wang, Chen Wu, Junliang Yoshikai, Naohiko Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile |
| title | Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile |
| title_full | Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile |
| title_fullStr | Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile |
| title_full_unstemmed | Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile |
| title_short | Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile |
| title_sort | stereoselective access to highly substituted vinyl ethers via trans difunctionalization of alkynes with alcohols and iodine iii electrophile |
| topic | Science::Chemistry Ethers Hydrocarbons |
| url | https://hdl.handle.net/10356/145625 |
| work_keys_str_mv | AT dingwei stereoselectiveaccesstohighlysubstitutedvinylethersviatransdifunctionalizationofalkyneswithalcoholsandiodineiiielectrophile AT chaijinkui stereoselectiveaccesstohighlysubstitutedvinylethersviatransdifunctionalizationofalkyneswithalcoholsandiodineiiielectrophile AT wangchen stereoselectiveaccesstohighlysubstitutedvinylethersviatransdifunctionalizationofalkyneswithalcoholsandiodineiiielectrophile AT wujunliang stereoselectiveaccesstohighlysubstitutedvinylethersviatransdifunctionalizationofalkyneswithalcoholsandiodineiiielectrophile AT yoshikainaohiko stereoselectiveaccesstohighlysubstitutedvinylethersviatransdifunctionalizationofalkyneswithalcoholsandiodineiiielectrophile |