- A novel transformation of primary amines to N-monoalkylhydroxylamines
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A novel transformation of primary amines to the corresponding N-monoalkylhydroxylamines is described. The three-step protocol involves selective mono-cyanomethylation of primary amines, regioselective formation of nitrones by m-CPBA oxidation, and hydroxylaminolysis of the nitrones with hydroxylamine hydrochloride. The method is applicable for a wide range of primary amines, including alkyl, benzyl, and chiral.
- Tokuyama,Kuboyama,Amano,Yamashita,Fukuyama
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p. 1299 - 1304
(2007/10/03)
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- The use of the cyanomethyl unit as a protecting group for phenols, amines and carbamates
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The use of the cyanomethyl unit as a protecting group for phenols, primary and secondary amines, and carbamates is described. Optimized conditions for formation and hydrolysis of cyanomethyl in the presence of the other hydrogenolysis-sensitive groups such as O- and N-benzyl groups are presented.
- Benarab,Boye,Savelon,Guillaumet
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p. 7567 - 7568
(2007/10/02)
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