Two-Step Asymmetric Synthesis of Disubstituted N-Tosyl Aziridines Having 98−100% ee: Use of a Phosphazene Base

Autor:	Vitomir Sunjić, Arlette Solladié-Cavallo, Richard Welter, Marin Roje
Rok vydání:	2004
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Chiral auxiliary Tosyl chemistry Ylide Stereochemistry Organic Chemistry Enantioselective synthesis Enantiomer Enantiomeric excess Chemical synthesis Phosphazene
Zdroj:	The Journal of Organic Chemistry. 69:1409-1412
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo035586x
Popis:	Unknown diaryl (1-3) and alkyl-phenyl (4, 5) N-tosyl aziridines have been successfully synthesized from pure (R,R,R,S(S))-(-)-sulfonium salt derived from Eliel's oxathiane, tosylimines 11a-f, and using a phosphazene base (EtP(2)) to generate the ylide. Both cis and trans aziridines have exceptionally high enantiomeric purities (98.7-99.9%). The (2R,3R)-configuration of trans-3 and the (2R,3S)-configuration of cis-4 have been determined by X-ray analysis using the Bijvoet method. The R-configuration found at C2 is consistent with the model and all previous results, therefore all trans-aziridines and cis-aziridines have been assigned the (2R,3R)- and the (2R,3S)-configurations, respectively. This two-step asymmetric synthesis can be easily used on gram quantities and involves no unstable/hazardous reagent. The chiral auxiliary is used in a stoichiometric amount but is recovered in high yield and reused.
Databáze:	OpenAIRE
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