ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Recently Viewed
You have not visited any articles yet, Please visit some articles to see contents here.
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2012, 77, 3, 1599-1604
RETURN TO ISSUEPREVNoteNEXT

Alkene Metathesis Approach to β-Unsubstituted Anti-Allylic Alcohols and Their Use in Ene–Yne Metathesis

View Author Information
Department of Chemistry, University at Buffalo, the State University of New York, Buffalo, New York 14260, United States
*E-mail: [email protected]
Cite this: J. Org. Chem. 2012, 77, 3, 1599–1604
Publication Date (Web):December 22, 2011
https://doi.org/10.1021/jo202398q
Copyright © 2011 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
1497
Altmetric
-
Citations
13
LEARN ABOUT THESE METRICS
Read OnlinePDF (494 KB)
Get e-Alerts
Supporting Info (1)»
SUBJECTS:

Abstract

Abstract Image

The synthesis of β-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction conjoined with a relay-type ring-closing alkene metathesis is reported. The metathesis step serves to remove a β-alkenyl group, which facilitated the aldol step. The β-substituted enals serve as acrolein surrogates. The products were employed in ene–yne cross metathesis.

Supporting Information

ARTICLE SECTIONS
Jump To

NMR spectroscopic data for new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 13 publications.

  1. Denis S. Baranov, Brian Gold, Sergei F. Vasilevsky, and Igor V. Alabugin . Divergent Cyclizations of 1-R-Ethynyl-9,10-anthraquinones: Use of Thiourea as a “S2–” Equivalent in an “Anchor-Relay” Addition Mediated by Formal C–H Activation. The Journal of Organic Chemistry 2013, 78 (5) , 2074-2082. https://doi.org/10.1021/jo302146r
  2. Joseph R. Clark, Jonathan M. French, Edgars Jecs, and Steven T. Diver . Geminal Alkene–Alkyne Cross Metathesis Using a Relay Strategy. Organic Letters 2012, 14 (16) , 4178-4181. https://doi.org/10.1021/ol301846q
  3. R.B. Lincoln. ene‐yne coupling. 2020https://doi.org/10.1002/9783527809080.cataz06363
  4. Nhan Do Van Thanh. 1,2-Anti aldol methodologies used in natural product synthesis. Tetrahedron 2020, 76 (4) , 130618. https://doi.org/10.1016/j.tet.2019.130618
  5. Hani Hassan. A Short and Efficient Total Synthesis of Ficuseptamines A and B. Molecules 2018, 23 (8) , 1865. https://doi.org/10.3390/molecules23081865
  6. Johan Bidange, Cédric Fischmeister, Christian Bruneau. Ethenolysis: A Green Catalytic Tool to Cleave Carbon-Carbon Double Bonds. Chemistry - A European Journal 2016, 22 (35) , 12226-12244. https://doi.org/10.1002/chem.201601052
  7. Sebastian Kriening, Athanasios Evagelou, Birgit Claasen, Angelika Baro, Sabine Laschat. Asymmetric Evans syn -Aldol Reactions of Terpene-Derived Enals: Scope and Limitations. European Journal of Organic Chemistry 2014, 2014 (30) , 6720-6733. https://doi.org/10.1002/ejoc.201402736
  8. James W. Herndon. The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2012. Coordination Chemistry Reviews 2014, 272 , 48-144. https://doi.org/10.1016/j.ccr.2014.02.026
  9. Steven T. Diver, Justin R. Griffiths. Ene-Yne Metathesis. 2014, 153-185. https://doi.org/10.1002/9781118711613.ch4
  10. S.T. Diver, J.R. Clark. 5.27 Ene–Yne Metathesis. 2014, 1302-1356. https://doi.org/10.1016/B978-0-08-097742-3.00528-0
  11. Steven T. Diver, Jonathan M. French. Ruthenium Carbenes. 2013, 404-451. https://doi.org/10.1002/9781118730379.ch13
  12. Steven B. Garber, Amir H. Hoveyda, R. Kashif M. Khan, Tyler J. Mann, Amir H. Hoveyda. Dichloro[[2-(1-methylethoxy- O )phenyl]-methylene] (tricyclohexylphosphine) Ruthenium. 2013https://doi.org/10.1002/047084289X.rn00129.pub2
  13. Joseph R. Clark, Jonathan M. French, Steven T. Diver. ChemInform Abstract: Alkene Metathesis Approach to β-Unsubstituted anti-Allylic Alcohols and Their Use in Ene-Yne Metathesis.. ChemInform 2012, 43 (22) , no-no. https://doi.org/10.1002/chin.201222041

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE