[reaction: see text] The N-chloramine salt of tert-butylsulfonamide has been shown to be an efficient nitrogen source and the terminal oxidant for catalytic aminohydroxylation and aziridination of olefins, resembling closely Chloramine-T by its behavior in these catalytic reactions. The sulfonyl-nitrogen bond in the product or its derivatives is easily cleaved under mild acidic conditions, allowing for facile liberation of the amino group.
An investigation into the asymmetric synthesis of 5-substituted
cyclohexenones via nucleophile
addition to (alkoxyarene)chromium tricarbonyl complexes is described.
Diastereoselectivity during
the nucleophile addition step was achieved using alkoxy substituents
derived from terpenoid
substrates as chiral auxiliaries. Selectivities as high as 24:1
were obtained when 2-phenylisoborneol
was used as the chiral auxiliary and as high as 17:1 using
3,3-(ethylenedioxy)isoborneol. The
absolute stereochemistry of the major products was assigned by
Mosher's method, after their
conversion to the corresponding cyclohexenol. A study of the
temperature dependence of the
nucleophile addition to alkoxytoluene complexes revealed a
thermodynamic preference for addition
ortho to the ether substituent.
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