Enantioselective “Clip-Cycle” Synthesis of Di-, Tri- and Spiro- Substituted Tetrahydropyrans

Paul Andrew Clarke; Khadra Alomari; Sai Pavan Chakravarthy; Bastien Duchadeau; Kristaps Ermanis

doi:10.1039/D2OB00023G

Enantioselective “Clip-Cycle” Synthesis of Di-, Tri- and Spiro- Substituted Tetrahydropyrans

Paul Andrew Clarke, Khadra Alomari, Sai Pavan Chakravarthy, Bastien Duchadeau, Kristaps Ermanis

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

-Unsaturated alcohols were “clipped” via alkene metathesis to a thioester activating group, which was followed by a chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization to yield tetrahydropyrans and spiro-tetrahydropyrans with excellent enantioselectivity. The mechanism and origin of the enantioselectivity was probed by DFT calculations and kinetic isotope studies, where there was excellent correlation between the computational and synthetic investigations

Original language	English
Pages (from-to)	1181-1185
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	6
DOIs	https://doi.org/10.1039/D2OB00023G
Publication status	Published - 13 Jan 2022

Bibliographical note

© The Royal Society of Chemistry 2022. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

Access to Document

10.1039/D2OB00023GLicence: CC BY

d2ob00023gFinal published version, 1.67 MBLicence: CC BY

1 Invited talk

Invited Research Seminar at the University of Birmingham
Clarke, P. A. (Invited speaker)
12 Jul 2022
Activity: Talk or presentation › Invited talk

1 Finished

Asymmetric Clip-Cycle Synthesis of THPs
Clarke, P. A. (Principal investigator), Alomari, K. (Student) & Chakravarthy, S. P. (Student)
1/01/17 → 31/12/23
Project: Other project › Miscellaneous project

Enantioselective Clip-Cycle Formation of THPs
Clarke, P. A. (Creator), Chakravarthy, S. P. (Contributor), Alomari, K. (Contributor) & Duchadeaau, B. (Contributor), University of York, 2021
DOI: 10.15124/8ff9123f-ee1a-4ae2-a60e-7626c989e5a0
Dataset

Cite this

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title = "Enantioselective “Clip-Cycle” Synthesis of Di-, Tri- and Spiro- Substituted Tetrahydropyrans",

abstract = "-Unsaturated alcohols were “clipped” via alkene metathesis to a thioester activating group, which was followed by a chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization to yield tetrahydropyrans and spiro-tetrahydropyrans with excellent enantioselectivity. The mechanism and origin of the enantioselectivity was probed by DFT calculations and kinetic isotope studies, where there was excellent correlation between the computational and synthetic investigations",

author = "Clarke, {Paul Andrew} and Khadra Alomari and Chakravarthy, {Sai Pavan} and Bastien Duchadeau and Kristaps Ermanis",

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AU - Alomari, Khadra

AU - Chakravarthy, Sai Pavan

AU - Duchadeau, Bastien

AU - Ermanis, Kristaps

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PY - 2022/1/13

Y1 - 2022/1/13

N2 - -Unsaturated alcohols were “clipped” via alkene metathesis to a thioester activating group, which was followed by a chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization to yield tetrahydropyrans and spiro-tetrahydropyrans with excellent enantioselectivity. The mechanism and origin of the enantioselectivity was probed by DFT calculations and kinetic isotope studies, where there was excellent correlation between the computational and synthetic investigations

AB - -Unsaturated alcohols were “clipped” via alkene metathesis to a thioester activating group, which was followed by a chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization to yield tetrahydropyrans and spiro-tetrahydropyrans with excellent enantioselectivity. The mechanism and origin of the enantioselectivity was probed by DFT calculations and kinetic isotope studies, where there was excellent correlation between the computational and synthetic investigations

U2 - 10.1039/D2OB00023G

DO - 10.1039/D2OB00023G

M3 - Article

SN - 1477-0520

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EP - 1185

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -

Enantioselective “Clip-Cycle” Synthesis of Di-, Tri- and Spiro- Substituted Tetrahydropyrans

Abstract

Bibliographical note

Access to Document

Activities

Invited Research Seminar at the University of Birmingham

Projects

Asymmetric Clip-Cycle Synthesis of THPs

Datasets

Enantioselective Clip-Cycle Formation of THPs

Cite this