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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 10
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Original Articles

Conjugate Addition of Anions of Protected Cyanohydrins to β-Nitro-Styrene and Some Synthetic Applications of the Resulting Adducts

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Pages 717-723 | Published online: 05 Dec 2006

References

  • Stork , G. and Maldonado , L. A. 1971 . J. Amer. Chem. Soc. , 93 : 5286 96, 5272 (1974)
  • Ferriño , M. Sc. M. Sc. December 1975 . December , in the First Chemical Congress of the North American Continent, México, D. F., A portion of this work was presented by, S. A. Ferriño and L. A. Maldonado, “A new synthesis of some α-methylene ketones”, abstract ORGA 42. At about the same time, Seebach reported the conjugate addition of the more popular acyl a-nion equivalents, the 1,3-dithiane anions, to a variety of nitro olefins: D. Seebach, H. F. Leitz and V. Ehrig, Chem. Ber., 108, 1924 (1975) and studied some transformations with the resulting adducts: D. Seebach, V. Ehrig, H. F. Leitz and R. Henning, Chem. Ber., 108, 1946 (1975). However, his results differ from that described in this paper and therefore, our work can be considered as complementary to the more extensive study of Seebach
  • All these α-methylene ketones showed a pair of singlets at 5.50–6.00 δ in their pmr spectra
  • Gras , J.-L . 1978 . Tetrahedron Letts. , 2111 : 2955 For another recent synthesis of α-methylene ketones see:
  • An important side reaction in this transformation is competitive HCN and HNO2 removal, previous, to the bis hydroxymethylation reaction to give the corresponding α-methylene ketone. Obviously, substrates with an alkaline stable carbonyl protecting group, should improve the yield in this step making more attractive this furane synthesis7
  • Pérez , S. S. January 1977 . Synthetic applications of γ-ketal nitro compounds , Chemistry thesis January ,
  • Unpublished work with H. Escalona
  • Pérez , S. S. and Maldonado , L. A. August 1977 . Ketals of β-nitro ketones. Formal total synthesis of juvabione , abstract 198 , August , Toluca, México : XII Congreso Mexicano de Quimica Pura Y Aplicada . The utility of ketals of β-nitro ketones as synthetic equivalents of the β-acyl vinyl anion (3-oxo-vinyl anion), has also been discovered by Bakuzis: P. Bakuzis, M. L. F. Bakuzis and T. F. Weingartner, Tetrahedron Letts., 2371 (1978)
  • Manjarrez , N. and Manjarrez , N. May 1977 . Synthesis of 13-oxi-prostanoids , Chemistry thesis May , Work in progress with
  • We thank Cámara Nacional de la Industria de Laboratorios Quimico Farmacéuticos for partial support of our work

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