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dc.contributor.authorTan, Ploypailin Siew Lingen_US
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.
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.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
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