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Asymmetric Synthesis of β-Substituted α-Amino Acids Using 2 H -Azirine-2-carboxylate Esters. Synthesis of 3,3-Disubstituted Aziridine-2-carboxylate Esters †

✍ Scribed by Davis, Franklin A.; Liang, Chang-Hsing; Liu, Hu


Book ID
120987076
Publisher
American Chemical Society
Year
1997
Tongue
English
Weight
185 KB
Volume
62
Category
Article
ISSN
0022-3263

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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