Applications of aziridinium ions. Selective syntheses of β-aryl-α,β-diamino esters

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1435-1437

  Chuang, Tsung Hsun ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZIRIDINE DERIVATIVE; ESTER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

AMINES; AZIRIDINES; ESTERS; MODELS, MOLECULAR;

EID: 0033523816     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990256d     Document Type: Article

References (28)

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21. + + 1, 35), 176 (100).
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23. + - Cl, 40), 172 (81).
24. Details of the crystal structure information can be obtained from the Director of the Cambridge Crystallographic Data Center, University of Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K.
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26. 2/hexane gave regioisomerically pure samples of 5b, 5c, 5d, and 5e with melting points of 64-66°C, 69-70°C, 106-108°C, and 137-138°C, respectively (see Supporting Information for spectral data on all products).
27. 3 (280 mg, 2.0 mmol) was added followed by tert-butylamine (530 μL, 365 mg, 5.0 mmol). The mixture was heated at 60°C (open to air) for 12 h. The same purification procedure as in ref 9 gave 340 mg (>99%) of regioisomers 5a and 6a (92:8).
28. 3CN (70 mL), and 1-phenylpiperazine (6.6 g, 6.2 mL, 40.8 mmol).