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2-Methyl N-(p-toluenesulfinyl)aziridine-2-carboxylic acid: Asymmetric synthesis of α-methylphenylalanine and α-methyl-β-phenylserine

✍ Scribed by Franklin A. Davis; Hu Liu; G. Venkat Reddy


Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
239 KB
Volume
37
Category
Article
ISSN
0040-4039

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Aziridine 2-carboxylate ester mediated a
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The highly stereoselective ring opening of N-tosylaziridine 2-carboxylate esters with LiAIH4 followed by oxidation of the ensuing syn alcohols results in a highly efficient 4 step asymmetric synthesis of a-methyl I~-amino acids from N-sulfinylaziridine 2-carboxylate esters.

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Aziridine 2-Carboxylate Ester Mediated Asymmetric Synthesis of α-Alkyl β-Amino Acids. -Highly stereoselective reductive ring opening of the N-tosylaziridines (II) with LiAlH4 followed by oxidation of the syn-amino alcohols (III) provides an efficient entry to the asymmetric synthesis of αmethyl β-am