Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/150700
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dc.contributor.authorTan, Ploypailin Siew Lingen_US
dc.date.accessioned2021-06-23T00:43:56Z-
dc.date.available2021-06-23T00:43:56Z-
dc.date.issued2021-
dc.identifier.citationTan, 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/10356/150700en_US
dc.identifier.urihttps://hdl.handle.net/10356/150700-
dc.description.abstractStereoselective 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.en_US
dc.language.isoenen_US
dc.publisherNanyang Technological Universityen_US
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0).en_US
dc.subjectScience::Chemistry::Organic chemistryen_US
dc.titleRegio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate esteren_US
dc.typeThesis-Master by Researchen_US
dc.contributor.supervisorChiba Shunsukeen_US
dc.contributor.supervisorNaohiko Yoshikaien_US
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.description.degreeMaster of Scienceen_US
dc.identifier.doi10.32657/10356/150700-
dc.contributor.supervisoremailShunsuke@ntu.edu.sg, NYOSHIKAI@ntu.edu.sgen_US
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item.grantfulltextembargo_20220527-
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