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

doi:10.3390/30300080

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

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

Tuvia Sheradsky* and Elliad R. Silcoff

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

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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

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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.

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