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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 8
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Original Articles

Synthesis of Optically Active (E)-γ-Hydroxy-α, β-unsaturated Nitriles

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Pages 1109-1113 | Received 23 Oct 1991, Published online: 23 Sep 2006

References

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  • Treatment of la with thionyl chloride (1.2 equiv) in the presence of 2 equiv triethylamine at 0°C for 10 min provided the cyclic sulfite 2a, which on exposure to 2 equiv LDA in THF at -78 °C for 30 min afforded 4a in 80 % overall yield
  • When the compound 1a was treated with 3 equiv NaH and excess dimethyl carbonate, 4a was obtained directly
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  • Le Merrer , Y. , Gravier-Pelletier , C. , Dumas , J. and Pepezay , J. C. 1990 . Tetrahedron Lett , 31 : 1003
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  • Dehydrations are normally carried out in two steps by first activating as acetate or sulfonate of the hydroxyl and then effecting elimination with base
  • Worbel , J. E. and Ganem , B. 1983 . J. Org. Chem , 48 : 3761 In the case of β-hydroxy lactone, one-pot dehydration by treatment with mesyl chloride in the presence of triethylamine is known, see
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