Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 24
518
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Development of a New α‐Aminonitrile Synthesis

, , &
Pages 4583-4590 | Received 24 Aug 2004, Published online: 10 Jan 2011

References

  • Strecker , A. 1850 . Justus Liebigs . Ann. Chem. , 75 : 27 – 45 .
  • Matier , W. L. , Owen , D. A. and Comer , W. T. 1973 . Antihypertensive Agents. Synthesis and Biological Properties of 2‐Amino‐4‐Aryl‐2‐Imidazolines . J. Med. Chem. , 16 : 901 – 908 .
  • Bigge , C. F. , Drummond , J. T. , Johnson , G. , Molone , T. , Probert , A. W. Jr. , Marcoux , F. W. , Coughenour , L. L. and Brahce , L. J. 1989 . Exploring of Phenyl‐Spaced 2‐Amino‐(5‐9)‐Phosphonoalkanoic Acids as Competitive N‐Methyl‐D‐aspartic Acid Antagonists . J. Med. Chem. , 32 : 1580 – 1590 .
  • Zimmerman , H. E. and Wright , C. W. 1992 . Triplet Photochemistry of Acyl and Imino Cyclopropenes. A Rearrangement To Afford Furans and Pyrroles: Reaction and Mechanism . J. Am. Chem. Soc. , 114 : 6603 – 6613 .
  • Eizember , R. F. and Ammons , A. S. 1976 . A Convenient Preparation of D‐(−)‐p‐Hydroxyphenylglycine . Org. Prep. Proced. Intl. , 8 : 149 – 153 .
  • Mai , K. and Patil , G. 1984 . Facile Synthesis of α‐Aminonitriles . Tetrahedron Lett. , 25 : 4583 – 4586 .
  • Zhu , J. , Beugelmans , R. , Bigot , A. , Singh , G. P. and Bois‐Choussy , M. 1993 . A Concise and Efficient Synthesis of Protected Actinoidic Acid, the Degradation Product of Vancomycin . Tetrahedron Lett. , 34 : 7401 – 7404 .
  • Mai , K. and Patil , G. 1985 . A Modified Strecker Synthesis . Org. Prep. Proced. Intl. , 17 : 183 – 186 .
  • Georgiadis , M. P. and Haroutounian , S. A. 1989 . A Facile and High‐Yield Synthesis of α‐Benzylaminonitriles by A Modified Strecker Reaction . Synthesis , : 616 – 618 .
  • Shafran , Y. M. , Bakulev , V. A. and Mokrushin , V. S. 1989 . Synthesis and Properties of α‐Aminonitriles . Russ. Chem. Rev. , 58 : 148 – 162 .
  • Chu , G. H. , Gu , M. , Gerard , B. , Salvino , J. and Dolle , R. E. Development of a New α‐Aminonitrile Synthesis . Abstracts of Papers, 224th ACS National Meeting of the American Chemical Society . August 18–22 2002 , Boston, MA. Washington, DC : American Chemical Society . ORGN‐713
  • Kruger , C. , Rochow , E. G. and Wannagat , U. 1963 . Silicon‐Nitrogen Compounds. XXIII. The Action of Sodium Bis(trimethylsilyl)amide on Benzophenone . Chem. Ber. , 96 : 2132
  • Chan , L.‐H. and Rochow , J. 1967 . Syntheses and Ultraviolet Spectra of N‐Organosilyl Ketimines . J. Organomet. Chem. , 9 : 231
  • Hart , D. J. and Kanai , K. 1982 . New Approach to Lythraceae Alkaloids: Total Synthesis of (±)‐Vertaline . J. Org. Chem. , 47 : 1555 – 1560 .
  • Hart , D. J. , Kanai , K. , Thomas , D. G. and Yang , T.‐K. 1983 . Preparation of Primary Amines and 2‐Azetidinones via N‐Trimethylsilyl Imines . J. Org. Chem. , 48 : 289 – 294 .
  • Hart , D. J. , Hong , W.‐P. and Hsu , L.‐Y. 1987 . Total Synthesis of (±)‐Lythrancepine II and (±)‐Lythrancepine III . J. Org. Chem. , 52 : 4665 – 4673 . (The reaction between N‐TMS imines and Grignard reagents was used for the preparation of benzylamine derivatives in the total synthesis of (±)‐vertaline, (±)‐lythrancepine II and III)
  • Cainelli , G. , Giacomini , D. , Panunzio , M. , Martelli , G. and Spunta , G. 1987 . β‐Lactams from Esters and Silylimines: A Revaluation. Synthesis of N‐Unsubstituted 4‐Alkyl‐β‐Lactams . Tetrahedron Lett. , 28 : 5369
  • Uyehara , T. , Suzuki , T. and Yamamoto , Y. 1989 . A Novel Method for Generation of Enolizable N‐Trimethylsilylaldimines and Application to β‐Lactam Synthesis . Tetrahedron Lett. , 30 : 4275
  • Cainelli , G. , Panunzio , M. and Giacomini , D. 1991 . Studies on N‐Metallo Imines: Synthesis of N‐Unsubstituted Aziridines from N‐Trimethylsilylimine and Lithium Enolates of α‐Halo Esters . Tetrahedron Lett. , 32 : 121 – 124 .
  • Cainelli , G. , Martelli , G. , Panunzio , M. and Spunta , G. 1993 . β‐Lactams from Ester Enolates and N‐(Trimethylsilyl)imines: A Simple Route to 1β‐Methyl PS‐5 . Gazzetta Chimica Italiana , 123 : 509 – 513 .
  • Gyenes , F. , Bergmann , K. E. and Welch , J. T. 1998 . Convenient Access to Primary Amines by Employing the Barbier‐Type Reaction of N‐(Trimethylsilyl)imines Derived from Aromatic and Aliphatic Aldehydes . J. Org. Chem. , 63 : 2824 – 2828 .
  • Ooi , T. , Takana , K. , Ichikawa , H. and Muruoka , K. 2001 . Zr(OBut)4 as An Effective Promoter for the Meerwein‐Ponndorf‐Verley Alkynylation and Cyanation of Aldehydes: Development of New Asymmetric Cyanohydrin Synthesis . Tetrahedron Lett. , 57 : 867 – 873 . (For the addition to aldehydes)
  • Lee , T. and Ahn , Y. 2002 . Enzymatic Introduction of Cyanide into Imine for Constructing Optically Active Compound by (R)‐Oxynitrilase in Almond Meal . Bull. Korean Chem. Soc. , 23 : 1490 – 1492 . (For the addition to imines)
  • Sundermeier , M. , Zapf , A. and Beller , M. 2003 . A Convenient Procedure for the Palladium‐Catalyzed Cyanation of Aryl Halides . Angew. Chem., Int. Ed. , 42 : 1661 – 1664 . (For the palladium catalyzed cyanation of aryl halides)
  • Lagu , B. , Dhar , T. G.M. , Nagarathnam , D. , Jeon , Y. T. , Marzabadi , M. R. , Wong , W. C. and Gluchowski , C. Oxazolidinones as α1A Receptor Antagonists . US Patent 6,159,990 . December 12, 2000 .
  • Buckland , P. R. Single Vessel Synthesis of Aminonitriles . US Patent 5,332,825 . July 26, 1994 .
  • E.R. Squibb and Sons, Inc., USA. 7‐Methoxypyridyl‐ and Phenylureidocephalosporins. NL 7609079, February 20, 1978

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.