N -(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

Since Garner's aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of -(1-phenylethyl)aziridine-2-carboxylates...

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Veröffentlicht in:Beilstein journal of organic chemistry 2019-07, Vol.15 (1), p.1722-1757
Hauptverfasser: Głowacka, Iwona E, Trocha, Aleksandra, Wróblewski, Andrzej E, Piotrowska, Dorota G
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Sprache:eng
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Zusammenfassung:Since Garner's aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of -(1-phenylethyl)aziridine-2-carboxylates, -carbaldehydes and -methanols in syntheses of approved drugs and potential medications as well as of natural products mostly alkaloids but also sphingoids and ceramides and their 1- and 3-deoxy analogues and several hydroxy amino acids and their precursors. Designed strategies provided new procedures to several drugs and alternative approaches to natural products and proved efficiency of a 2-substituted -(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.15.168