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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 15, 1985 - Issue 7
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Original Articles

Synthesis of a Chiral Bicyclo[4.1.0] Allylic Nitrile Via Reductive Cyclization of a Dienyl Nitrile

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Pages 549-567 | Published online: 05 Dec 2006

References

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  • Compound 19 was found to be contaminated with compound 20, the product of quenching of the anion of 8 with ethylene dibromide; 20 was synthesized separately from 8 and IR, NMR, mass and CMR were obtained (See experimental)
  • Metalation of the mixture with KDA at -78°C and subsequent warming of the reaction mixture to -20°C, afforded a ratio greater than 12:1 of 8 to 19 respectively
  • Arseniyadis , S. , Kyler , K. S. and Watt , D. S. 1984 . Organic Reactions , Vol. 31 , New York : John Wiley . For a comprehensive review on the chemistry of nitrile-stabilized carbanions see
  • Extensions of this strategy will be reported in due course
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  • We have observed that the quality of the triethylamine is very crucial in this reaction. One month old triethylamine slowed the reaction down and stopped it from going to completion even when more Pd[0] catalyst was added

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