Molecules 1998, 3(3), 80-87; doi:10.3390/30300080

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

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
PDF Full-text Download PDF Full-Text [43 KB, uploaded 10 October 2008 14:35 CEST]
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

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

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.

AMA Style

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

Chicago/Turabian Style

Sheradsky, Tuvia; Silcoff, Elliad R. 1998. "Synthesis of (2R,5R)-2-Amino-5-Hydroxyhexanoic Acid by Intramolecular Cycloaddition." Molecules 3, no. 3: 80-87.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert