Highly Enantioselective Construction of Tertiary Thioethers and Alcohols via Phosphine-Catalyzed Asymmetric γ-Addition reactions of 5H-Thiazol-4-ones and 5H-Oxazol-4-ones: Scope and Mechanistic Understandings
dc.contributor.author | Wang, Tianli | |
dc.contributor.author | Yu, Zhaoyuan | |
dc.contributor.author | Hoon, Ding Long | |
dc.contributor.author | Huang, Kuo-Wei | |
dc.contributor.author | Lan, Yu | |
dc.contributor.author | Lu, Yixin | |
dc.date.accessioned | 2015-06-10T18:45:35Z | |
dc.date.available | 2015-06-10T18:45:35Z | |
dc.date.issued | 2015 | |
dc.identifier.citation | Highly Enantioselective Construction of Tertiary Thioethers and Alcohols via Phosphine-Catalyzed Asymmetric γ-Addition reactions of 5H-Thiazol-4-ones and 5H-Oxazol-4-ones: Scope and Mechanistic Understandings 2015 Chem. Sci. | |
dc.identifier.issn | 2041-6520 | |
dc.identifier.issn | 2041-6539 | |
dc.identifier.doi | 10.1039/C5SC01614B | |
dc.identifier.uri | http://hdl.handle.net/10754/556699 | |
dc.description.abstract | Phosphine-catalyzed highly enantioselective γ-additions of 5H-thiazol-4-ones and 5H-oxazol-4-ones to allenoates have been developed for the first time. With the employment of amino-acid derived bifunctional phosphines, a wide range of substituted 5H-thiazol-4-one and 5H-oxazol-4-one derivatives bearing heteroarom (S or O)-containing tertiary chiral centers were constructed in high yields and excellent enantioselectivities. The reported method provides a facile access to enantioenriched tertiary thioether/alcohols. The mechanism of γ-addition reaction was investigated by performing DFT calculations, and the hydrogen bonding interactions between the Brønsted acid moiety of the phosphine catalysts and the “C=O” unit of donor molecules were shown to be crucial in asymmetric induction. | |
dc.publisher | Royal Society of Chemistry (RSC) | |
dc.relation.url | http://pubs.rsc.org/en/Content/ArticleLanding/2015/SC/C5SC01614B | |
dc.rights | Archived with thanks to Chem. Sci. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. http://creativecommons.org/licenses/by/3.0/ | |
dc.title | Highly Enantioselective Construction of Tertiary Thioethers and Alcohols via Phosphine-Catalyzed Asymmetric γ-Addition reactions of 5H-Thiazol-4-ones and 5H-Oxazol-4-ones: Scope and Mechanistic Understandings | |
dc.type | Article | |
dc.contributor.department | Chemical Science Program | |
dc.contributor.department | Homogeneous Catalysis Laboratory (HCL) | |
dc.contributor.department | KAUST Catalysis Center (KCC) | |
dc.contributor.department | Physical Science and Engineering (PSE) Division | |
dc.identifier.journal | Chem. Sci. | |
dc.eprint.version | Publisher's Version/PDF | |
dc.contributor.institution | Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore. | |
dc.contributor.institution | School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, P. R. China | |
kaust.person | Huang, Kuo-Wei | |
refterms.dateFOA | 2018-06-14T07:09:43Z |
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