Ring opening of unprotected aziridines by zinc selenolates in a biphasic system
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Acknowledgments
The authors thank CNPq, Capes, INCT-Catálise, and FAPERGS for financial support. S.M.S. thanks TWAS-CNPq for the PhD fellowship.
References and notes (13)
- et al.
J. Am. Chem. Soc.
(1960) - et al.
Adv. Strain. Interest. Org. Mol.
(2000)et al.Prog. Heterocycl. Chem.
(2001) - et al.
J. Am. Chem. Soc.
(1973)et al.Selenium in Natural Products Synthesis
(1984)Organoselenium Chemistry
(1987)Organoselenium Chemistry: A Practical Approach
(1999)Organoselenium Chemistry—Modern Developments in Organic Synthesis
(2000) - et al.
J. Am. Chem. Soc.
(1972)et al.Chem. Ber.
(1972)et al.Angew. Chem., Int. Ed.
(1974)J. Org. Chem.
(1975)et al.J. Am. Chem. Soc.
(1975)et al.Tetrahedron Lett.
(1976)et al.Tetrahedron Lett.
(1976)et al.Synth. Commun.
(1994)et al.Synlett
(1997)et al.Synthesis
(1998)et al.J. Org. Chem.
(2003)et al.Eur. J. Org. Chem.
(2003)et al.Synlett
(2006) Tetrahedron
(1999)Angew. Chem., Int. Ed.
(2000)et al.Synlett
(2006)et al.Curr. Org. Chem.
(2006)- et al.
Tetrahedron Lett.
(2006)et al.Tetrahedron Lett.
(2006)et al.Tetrahedron Lett.
(2007)et al.J. Am. Chem. Soc.
(2008)et al.Tetrahedron: Asymmetry
(2008)et al.Tetrahedron: Asymmetry
(2008)
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2019, Bioorganic ChemistryCitation Excerpt :Following the general procedure, 1,2-diphenylditellane 6a (41 mg, 0.1 mmol) and (S)-2-benzylaziridine 2b (32 mg, 0.24 mmol) gave, after purification by flash column chromatography (petroleum ether:EtOAc 1:1), (S)-1-phenyl-3-(phenyltellanyl)propan-2-amine 7f (39 mg, 57%). All recorded spectroscopic data matched those reported in the literature [26]. Following the general procedure, benzeneselenol 4a (41 mg, 0.1 mmol) and (S)-2-isopropylaziridine 2c (26 mg, 0.30 mmol) gave, after purification by flash column chromatography (petroleum ether:EtOAc 1:1), (S)-3-methyl-1-(phenyltellanyl)butan-2-amine 7g (35 mg, 60%).
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2019, Advances in Heterocyclic ChemistryCitation Excerpt :Toward this goal, Nonn et al. have employed difluorosulfiliminium tetrafluoroborate (XtelFluor-E) for regioselective selective fluoride opening of aziridines 296 with the neighboring group assistance of the sulfonamide furnishing fluorinated diamino acid derivatives 297 (Scheme 96) (2015OL1074). The N-unprotected 2-benzylaziridine 298 reacts with diaryl and dialkyl diselenides 300 in the presence of zinc dust as reducing agent in Et2O-HCl biphasic system to furnish β-selenoamines 301 (Scheme 97) (2009TL2309). The procedure involves the addition of zinc dust to the diselenide under acidic conditions converting it into the corresponding selenolate 300, followed by the addition of aziridine 298.
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2018, Coordination Chemistry ReviewsCitation Excerpt :Aziridine ring was activated by protonation with HCl; the resulting salt reacted with zinc selenolate in the aqueous layer. Reaction proceeded regioselectively, the products were formed by selenolate attack on the less-hindered aziridine carbon [53]. Properties of reaction (b) might be similar to reaction (a), but no information was provided in Ref. [54].