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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 14
62
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Original Articles

Reactions of Trimethylsilyl Cyanide with α-Keto Esters: Selective Preparation of Either Methyl 4-(Trimethyl-silyl) oxy-4-cyano-2-oxopentanoate or Methyl 2-(Trimethylsilyl) Oxy-2-cyano-4-oxopentanoate

Pages 1291-1297 | Published online: 06 Dec 2006

References

  • Evans , D. A. , Truesdale , L. K. and Carroll , G. L. J. 1973 . Chem. Soc. Chem. Commun. , 55.
  • Reactions carried out without silica gel were considerably slower and less clean. Some care is required to prevent further hydrolysis to the unstable cyanohydrin.
  • Hangauer , W. J. 1983 . D. G. Tetrahedron Lett. , 24 : 4559 Recent examples of catalyzed reactions of α-keto esters with TMSCN: GreenleeMukaiyama, T.; Oriyama, T.; Murakami, M. Chemistry Lett. 1983, 985 and reference 5.
  • The first step in the reaction of 3 with TMSCN, with or without a catalyst, involves the formation of the TMS enol ether i and HCN. Work is underway to delineate the mechanism of the conversion of i into either 4 or 2.
  • Ojima , I. and Inaba , S. 1978 . Chem. Abstr. , 89 : 109942x . Japan. Kokai 78 34,729.
  • This is contribution UNH NP-JR-SG-84-9 from the University of New Hampshire Sea Grant Program.

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