Aminohydroxylation of olefins with tert-alkyl sulfonamides

Details Aminohydroxylation of olefins with tert-alkyl sulfonamides Aminohydroxylation of olefins with tert-alkyl sulfonamides

1998-08-21

1999-12-28

McKane, Joseph K.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20324

Patent

active

06008376&

ABSTRACT:
Tert-alkyl sulfonamides chloramine salts are used as nitrogen sources in the catalytic aminohydroxylation and/or aziridination of olefins. The tert-alkyl sulfonamides chloramine salts are close to Chloramine T with respect to their reactivity as nitrogen sources with olefins. However, unlike the tosyl sulfonyl amine group of Chloramine T, the resulting t-alkyl sulfonylamino functionalities can be easily converted to an unprotected amine under mild acidic conditions making the method a simple and cost efficient approach for producing unsubstituted hydroxy amine and/or aziridine products.

REFERENCES:
CA70: 86837 Substituted aziridines. Relative rates . . . opening. Stephens et al. 1969.
King, et al., "tert-Butyl Cation Formation in the Hydrolysis of 2-Methyl-2-propanesulfonyl Chloride, the Simplest Tertiary Alkanesulfonyl Chloride", J. Org. Chem., 60:2831-2834 (1995).
Bruncko, et al., "Allylic Amination and 1,2-Diamination with a Modified Diimidoselenium Reagent", Angew. Chem. Int. Ed. Engl., 35(4):454-456 (1996).
Li, et al., "Catalytic Asymmetric Aminohydroxylation (AA) of Olefins", Angew. Chem. Int. Ed. Engl., 35(4):451-454 (1996).
Rubin, et al., "A Highly Efficient Aminohydroxylation Process", Angew. Chem. Int. Ed. Engl., 36(23):2637-2640 (1997).
Sun, et al., "tert-Butylsulfonyl (Bus), a New Protecting Group for Amines", J. Org. Chem., 62:8604-8608 (1997).

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