Synergistic substrate and catalyst effects in the addition of trimethylsilyl cyanide to imines derived from lactic acid

TETRAHEDRON

卷:75

Article

Fields, Alexander M.¹  Jones, Simon¹ 

[1] Univ Sheffield, Dept Chem, Dainton Bldg,Brook Hill, Sheffield S3 7HF, S Yorkshire, England

关键词: Lactimine;    Strecker reaction;    Trimethylsilyl cyanide;   

DOI  :  10.1016/j.tet.2019.04.067

来源: Elsevier

【 摘 要 】

Trimethylsilylcyanide was added to various imines derived from (2S)-ethyl lactate in the presence of Lewis acids to provide both syn- and anti- beta-hydroxy-alpha-aminonitrile stereoisomers. Syn-products were found to be the major in most instances, however, anti-products were formed in good yield and selectivity in the presence of ZnI2 & BF3 center dot OEt2 and N-(-)-alpha-methylbenzyl substituents via double stereo differentiation. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

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