Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester
Stereoselective synthesis of tetrasubstituted alkenes has been one of the most challenging subjects in synthetic organic chemistry. Regio- and stereoselective difunctionalization of readily available alkynes represents a conceptually straightforward approach toward this goal. In this Masters study,...
| Main Author: | |
|---|---|
| Other Authors: | |
| Format: | Thesis-Master by Research |
| Language: | English |
| Published: |
Nanyang Technological University
2021
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/150700 |
| _version_ | 1826121145806487552 |
|---|---|
| author | Tan, Ploypailin Siew Ling |
| author2 | Chiba Shunsuke |
| author_facet | Chiba Shunsuke Tan, Ploypailin Siew Ling |
| author_sort | Tan, Ploypailin Siew Ling |
| collection | NTU |
| description | Stereoselective synthesis of tetrasubstituted alkenes has been one of the most challenging subjects in synthetic organic chemistry. Regio- and stereoselective difunctionalization of readily available alkynes represents a conceptually straightforward approach toward this goal. In this Masters study, I have developed such an alkyne difunctionalization reaction using a hypervalent iodine reagent as an electrophile and a phosphate ester as a nucleophile. Thus, a three-component reaction involving an internal alkyne, benziodoxole triflate (BXT), and triethyl phosphate or related phosphate ester proceeds smoothly at room temperature, resulting in trans-addition of the benziodoxole (BX) and phosphate groups. The reaction has proved applicable to a variety of symmetrical and unsymmetrical internal alkynes, thus affording the corresponding β-λ3-iodanyl alkenyl phosphates in a regio- and stereoselective fashion. The BX and phosphate groups of the product can be utilized for sequential cross-coupling, thus allowing for the stereoselective synthesis of all-carbon tetrasubstituted alkenes. |
| first_indexed | 2024-10-01T05:27:56Z |
| format | Thesis-Master by Research |
| id | ntu-10356/150700 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:27:56Z |
| publishDate | 2021 |
| publisher | Nanyang Technological University |
| record_format | dspace |
| spelling | ntu-10356/1507002023-02-28T23:45:58Z Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester Tan, Ploypailin Siew Ling Chiba Shunsuke Naohiko Yoshikai School of Physical and Mathematical Sciences Shunsuke@ntu.edu.sg, NYOSHIKAI@ntu.edu.sg Science::Chemistry::Organic chemistry Stereoselective synthesis of tetrasubstituted alkenes has been one of the most challenging subjects in synthetic organic chemistry. Regio- and stereoselective difunctionalization of readily available alkynes represents a conceptually straightforward approach toward this goal. In this Masters study, I have developed such an alkyne difunctionalization reaction using a hypervalent iodine reagent as an electrophile and a phosphate ester as a nucleophile. Thus, a three-component reaction involving an internal alkyne, benziodoxole triflate (BXT), and triethyl phosphate or related phosphate ester proceeds smoothly at room temperature, resulting in trans-addition of the benziodoxole (BX) and phosphate groups. The reaction has proved applicable to a variety of symmetrical and unsymmetrical internal alkynes, thus affording the corresponding β-λ3-iodanyl alkenyl phosphates in a regio- and stereoselective fashion. The BX and phosphate groups of the product can be utilized for sequential cross-coupling, thus allowing for the stereoselective synthesis of all-carbon tetrasubstituted alkenes. Master of Science 2021-06-23T00:43:56Z 2021-06-23T00:43:56Z 2021 Thesis-Master by Research Tan, P. S. L. (2021). Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester. Master's thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/150700 https://hdl.handle.net/10356/150700 10.32657/10356/150700 en This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0). application/pdf Nanyang Technological University |
| spellingShingle | Science::Chemistry::Organic chemistry Tan, Ploypailin Siew Ling Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester |
| title | Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester |
| title_full | Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester |
| title_fullStr | Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester |
| title_full_unstemmed | Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester |
| title_short | Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester |
| title_sort | regio and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester |
| topic | Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/150700 |
| work_keys_str_mv | AT tanploypailinsiewling regioandstereoselectivealkynedifunctionalizationbyusingbenziodoxoletriflateandphosphateester |