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Asymmetric synthesis of α-amino acids via chiral N-alkylidenesulfinamides

✍ Scribed by Duy H. Hua; Nadege Lagneau; Hui Wang; Jinshan Chen

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
226 KB
Volume
6
Category
Article
ISSN
0957-4166

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✦ Synopsis

SR)-(-)-N-[1-(Triethoxymethyl)ethylidene]-p-toluenesulfinamide

(2) was synthesized from the addition reaction of triethoxyacetonitrile with MeLi followed by (+)-(R)-d-menthyl p-toluenesulfinate (1R). Sulfinimine 2 underwent complete stereoselective reduction with 9-BBN and addition reaction with allylmagnesium bromide. Optically pure a-amino acids were synthesized from these adducts by simple hydrolysis.

Chiral N-benzylidene-and N-alkylidenesulfinamides have been synthesized by four different methods:

(i) reactions of organometallic reagents with benzonitrile followed by (-)-l-menthyl (S)-p-toluenesulfinate (1S); l

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