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Title: | Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester | Authors: | Tan, Ploypailin Siew Ling | Keywords: | Science::Chemistry::Organic chemistry | Issue Date: | 2021 | Publisher: | Nanyang Technological University | Source: | 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 | Abstract: | 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. | URI: | https://hdl.handle.net/10356/150700 | DOI: | 10.32657/10356/150700 | Rights: | This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0). | Fulltext Permission: | embargo_20220527 | Fulltext Availability: | With Fulltext |
Appears in Collections: | SPMS Theses |
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Final thesis-ploy_ver.8-amended.pdf Until 2022-05-27 | 1.68 MB | Adobe PDF | Under embargo until May 27, 2022 |
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