Next Article in Journal
Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones
Previous Article in Journal
Synthesis of Novel Fused Heterocycles Based on Pyrano[2,3-c]pyrazole
Molecules 1998, 3(3), 80-87; doi:10.3390/30300080
Article

Synthesis of (2R,5R)-2-Amino-5-Hydroxyhexanoic Acid by Intramolecular Cycloaddition

*  and
Department of Organic Chemistry, the Hebrew University, Jerusalem 91904, Israel
* Author to whom correspondence should be addressed.
Received: 15 January 1998 / Accepted: 23 February 1998 / Published: 24 February 1998
Download PDF [43 KB, uploaded 18 June 2014]

Abstract

The title compound was synthesized from sorbic acid by an eight step sequence. The key step was the stereospecific intramolecular Diels-Alder reaction of the acylnitroso derivative of N-sorbyl-L-proline (5). L-Proline served as a temporary tether which directed both the stereochemistry and the regiochemistry of the cycloaddition.
Keywords: Intramolecular cycloaddition; enantiospecifity; proline; acylnitroso Intramolecular cycloaddition; enantiospecifity; proline; acylnitroso
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Sheradsky, T.; Silcoff, E.R. Synthesis of (2R,5R)-2-Amino-5-Hydroxyhexanoic Acid by Intramolecular Cycloaddition. Molecules 1998, 3, 80-87.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert