Aziridination of olefins

Details Aziridination of olefins Aziridination of olefins

1998-06-15

1999-07-27

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

518969, C07D20302, C07D20308

Patent

active

059292520

ABSTRACT:
A method for the direct aziridination of olefins as well as a wide range of allylic alcohols employs phenyltrimethylammonium tribromide (PTAB) as a general and effective catalyst and N-sodio-N-chloro sulfonamides, chloramine salts, as the nitrogen source.

REFERENCES:
Hassner et al., "The Reduction of Beta-Iodo Azides. A Stereospecific Synthesis of Aziridines," J. Am. Chem. Soc., vol. 91, No. 18, pp. 5046-5054, Aug. 27, 1969.
Atkinson, et al., "Aziridination of Cyclohex-2-en-1-ol and Geraniol: Comparison with Epoxidation", J. Chem. Soc., Chem. Commun., 624 (1988).
Evans, et al., "Copper-Catalyzed Aziridination of Olefins by (N-(p-Toluenesulfonyl)imino)phenyliodinane", J. Org. Chem., 56:6744 (1991).
Evans, et al., "Bis(oxazoline)-Copper Complexes as Chiral Catalysts for the Enantioselective Aziridination of Olefins", J. Am. Chem. Soc., 115:5328 (1993).
Li, et al., "Asymmetric Alkene Aziridination with Readily Available Chiral Diimine-Based Catalysts", J. Am. Chem. Soc., 115:5326 (1993).
Lowenthal, et al., "Asymmetric Copper-Catalyzed Cyclopropanation of Trisubstituted and Unsymmetrical cis-1,2-Disubstituted Olefins: Modified Bis-Oxazoline Ligands", Tetrahedrwon Leters, 32(50):7373 (1991).
Mansuy, et al., "Iron- and Manganese-porphyrin Catalysed Aziridination of Alkenes by Tosyl- and Acyl-iminoiodobenzene", J. Chem. Soc., Chem. Commun., 1161 (1984).
Nishikori, et al., "Catalytic and Highly Enantioselective Aziridination of Styrene Derivatives", Tetrahedron Letters, 37(51):9245 (1996).
Osborn, et al., "The Asymmetric Synthesis of Aziridines", Tetrahedon: Asymmetry, 8(11):1693 (1997).
Sodergren, et al., "Preparation and Evaluation of Nitrene Precursors (PhI=NSO2Ar) for the Copper-Catalyzed Aziridination of Olefins", Tetrahedron Letters, 38(39):6897 (1997).
Vedejs, et al., "Synthesis of N-Methoxy and N-H Aziridines from Alkenes", Tetrahedron Letters, 33(23):3261 (1992).

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