Highly diastereoselective addition of trimethylsilyl cyanide to chiral hydrazones in the presence of Et(2)AlCl

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Chiral hydrazones, synthesized from (S)-1-amino-2-methoxymethylindoline and aliphatic aldehydes, reacted with trimethylsilyl cyanide in the presence of diethylaluminium chloride in CH2Cl2 at -78 degrees C to give chiral alpha-hydrazinonitriles with high diastereoselectivity (up to 96% de). Copyright (C) 1996 Elsevier Science Ltd.
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Issue Date
1996-10
Language
English
Article Type
Article
Keywords

AMINO-ACIDS; STRECKER SYNTHESIS; SCHIFF-BASES

Citation

TETRAHEDRON LETTERS, v.37, no.43, pp.7795 - 7796

ISSN
0040-4039
DOI
10.1016/0040-4039(96)01780-7
URI
http://hdl.handle.net/10203/73189
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