Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 24, Pages 6008-6014Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900210
Keywords
asymmetric catalysis; enantioselectivity; ketimines; sodium; Strecker reaction
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Funding
- National Natural Science Foundation of China [20732003, 20602025]
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A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed. When 10 mol% BNPNa (BNP=1,1'-binaphthyl-2,2'-diylphosphate) prepared in situ and 10 mol % para-test-butyl-ortho-adamantylphenol (PBAP) were introduced into the reaction, up to 96% yield and up to 95% ee (ee = enantiomeric excess) were obtained. Both aliphatic and aromatic ketimines, especially sterically bulky cyclic ketimines derived from beta-acetonaphthone, alpha-indanone, and a-tetralone were found suitable for this reaction. On the basis of the experimental results and previous reports, trimethylsilyl cyanide (TMSCN) was indicated to be the real reactive nucleophile despite the existence of PBAP, and a possible working model was proposed to explain the origin of the asymmetric induction. The facile availability of 1,1'-binaphthy1-2,2'-diylphosphoric acid (BNPH) and the simplicity of the procedure are beneficial for practical applications.
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