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Selective reaction of amino acid sulfoximines with nitrous acid; facile stereospecific conversion to amino acid sulfoxides

✍ Scribed by Ralph A. Stephani; Alton Meister


Book ID
104243359
Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
216 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis


N-Unsubstituted sulfoximines of amino acids can be readily converted to the corresponding amino acid sulfoxides in high yields by treatment with stoichiometric quantities of nitrous acid. Under the conditions employed, reaction with L-methionine-S (or R)-sulfoximine is specific for the sulfoximine nitrogen atom, and no reaction occurs ot the a-amino group. Conversion to the sulfoxide proceeds with complete retention


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## Abstract A five‐step one‐pot procedure is presented to convert N‐Boc protected amino acids to N‐phthaloyl propargylic amines.