Stereoselective Synthesis of (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid via C–H Insertion of Alkylidenecarbene

Susumu OHIRADepartment of Biological Chemistry, Faculty of Science, Okayama University of Science1-1 Ridai-cho, Okayama 700-0005, Japan

Megumi AKIYAMADepartment of Biological Chemistry, Faculty of Science, Okayama University of Science1-1 Ridai-cho, Okayama 700-0005, Japan

Kumiko KAMIHARADepartment of Biological Chemistry, Faculty of Science, Okayama University of Science1-1 Ridai-cho, Okayama 700-0005, Japan

Yuichi ISODADepartment of Biological Chemistry, Faculty of Science, Okayama University of Science1-1 Ridai-cho, Okayama 700-0005, Japan

Atsuhito KUBOKIDepartment of Biological Chemistry, Faculty of Science, Okayama University of Science1-1 Ridai-cho, Okayama 700-0005, Japan

Abstract

(1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (ACPD), a potent agonist of metabotropic glutamate receptors, was synthesized from L-serine. The chiral quaternary center was constructed by C–H insertion of the alkylidenecarbene, this being generated by the reaction between lithiotrimethylsilyldiazomethane and the corresponding ketone.

Keywords

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Stereoselective Synthesis of (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid via C–H Insertion of Alkylidenecarbene

Information for

Open access

Opportunities

Help and information

Stereoselective Synthesis of (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid via C–H Insertion of Alkylidenecarbene

Abstract

Reprints and Corporate Permissions

Academic Permissions

Related research

To cite this article:

Download citation

Information for

Open access

Opportunities

Help and information

Keep up to date

Your download is now in progress and you may close this window

Login or register to access this feature