Show simple item record

dc.contributor.authorWang, Tianli
dc.contributor.authorYu, Zhaoyuan
dc.contributor.authorHoon, Ding Long
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorLan, Yu
dc.contributor.authorLu, Yixin
dc.date.accessioned2015-06-10T18:45:35Z
dc.date.available2015-06-10T18:45:35Z
dc.date.issued2015
dc.identifier.citationHighly 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.issn2041-6520
dc.identifier.issn2041-6539
dc.identifier.doi10.1039/C5SC01614B
dc.identifier.urihttp://hdl.handle.net/10754/556699
dc.description.abstractPhosphine-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.publisherRoyal Society of Chemistry (RSC)
dc.relation.urlhttp://pubs.rsc.org/en/Content/ArticleLanding/2015/SC/C5SC01614B
dc.rightsArchived 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.titleHighly 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.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalChem. Sci.
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
dc.contributor.institutionSchool of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, P. R. China
kaust.personHuang, Kuo-Wei
refterms.dateFOA2018-06-14T07:09:43Z


Files in this item

Thumbnail
Name:
c5sc01614b.pdf
Size:
1.992Mb
Format:
PDF
Description:
Main article
Thumbnail
Name:
c5sc01614b1.pdf
Size:
7.159Mb
Format:
PDF
Description:
Supplemental files

This item appears in the following Collection(s)

Show simple item record