Hydroxyamines optically active

Chiral carbamates were prepared from racemic or optically active secondary alcohols A H and used to determine the induced diastereoselectivity of the osmium-catalyzed hydroxyamination reaction93. 

Similar treatment of cyclohexene with Chloramine-T (sodium /7-toluenesulfonchlo-ramide) in a polar solvent such as BuOH in the presence of a catalytic amount of OSO4 gives the optically active hydroxyaminated cyclohexane in good yield (80%) (eq (78)) [259]. 

The transition metal-catalyzed asymmetric Michael addition reaction was first reported by Brunner employing the complex of Co(acac)2 and (S,S)-l,2-diphe-nyl-l,2-ethylenediamine (Scheme 12) [59, 60]. An enantiomeric excess of 66% was attained in the reaction of 6 and 7 giving R)-8 at -50 C in toluene. The dimeric copper complex 65 derived from salicylaldehyde and optically active (S)-hydroxyamines also promoted the reaction giving (S)-8 in 75% ee [61, 62, 63]. The second hydroxy group is considered to occupy the axial position of the monomeric intermediate. 

Palacz, Z. N-Benzylideneamino Acid N-Oxides and Their Use in the Synthesis of N-Benzylidenepeptide N-Oxide Esters and in the Synthesis of Optically Active N-Hydroxyamines. Ph. D. Thesis, University of Gdansk 1978. 

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