STEREOCHEMISTRY IN THE PROTONATION OF ENOLATES GENERATED FROM 2-SUBSTITUTED 2-CYCLOPENTEN-1-ONES BY THE 1, 4-ADDITION OF TRIALKYLSILYL AND TRIBUTYLSTANNYL ANIONS

References

• Posner , G. H. 1972 . Org. React. , Edited by: Dauben , W. G. Vol. 19 , 1 New York : John Wiley . D. A. Evans, in “Asymmetric Synthesis,” edited by J. D. Morrison (New York, Academic Press, 1984), Vol. 3, p. 1; J. A. Kozlowski, in “Comprehensive Organic Synthesis,” edited by B. M. Trost, (Oxford, Pergamon, 1991), Vol. 4, p. 169
   Google Scholar
• Toru , T. , Yamada , Y. , Ueno , T. , Maekawa , E. and Ueno , Y. 1988 . J. Am. Chem. Soc. , 110 : 4815
   Google Scholar
• Kusuda , S. , Watanabe , Y. , Ueno , Y. and Toru , T. 1991 . Tetrahedron Lett. , 32 : 1325
   Google Scholar
• Kusuda , S. , Watanabe , Y. , Ueno , Y. and Toru , T. 1992 . J. Org. Chem. , 97 : 3145
   Google Scholar
• Watanabe , Y. , Ueno , Y. and Toru , T. 1993 . Bull. Chem. Soc., Jpn. , 66 : 2042
   Google Scholar
• Kusuda , S. , Ueno , Y. and Toru , T. 1993 . Bull. Chem. Soc., Jpn. , 66 : 2720
   Google Scholar
• Kusuda , S. , Ueno , Y. , Hagiwara , T. and Toru , T. 1993 . J. Chem. Soc., Perkin Trans., 1 , : 1981
   Google Scholar
• Liotta , D. , Saindane , M. , Barnum , C. and Zima , G. 1985 . Tetrahedron , 81 : 4881
   Google Scholar
• Still , W. C. 1976 . J. Org. Chem. , 81 : 3063 For the 1,4-addition of trialkylsilyl anion, see: (a)
   Google Scholar
• Fleming , I. and Waterson , D. 1984 . J. Chem. Soc., Perkin Trans., 1 , : 1805 – 1809 .
   Google Scholar
• Bernhard , W. , Fleming , I. and Waterson , D. 1984 . J. Chem. Soc., Chem. Commun. , 28
   Google Scholar
• Ager , D. J. , Fleming , I. and Patei , S. K. 1981 . J. Chem. Soc., Perkin Trans., 1 , : 2520
   Google Scholar
• Fleming , I. and Percival , A. 1978 . J. Chem. Soc., Chem. Commun. , : 177
   Google Scholar
• Sharma , S. and Oehlschlager , A. C. 1989 . Tetrahedron , 89 : 557
   Google Scholar
• Sharma , S. and Oehlschlager , A. C. 1991 . J. Org. Chem. , 96 : 770
   Google Scholar
• Takaki , K. , Maeda , T. and Ishikawa , M. 1989 . J. Org. Chem. , 98 : 58
   Google Scholar
• Chapdelaine , M. J. and Hulce , M. 1990 . Org. React. , 38 : 225
   Google Scholar
• Zima , G. and Liotta , D. 1979 . Synth. Commun. , 9 : 697
   Web of Science ®Google Scholar
• Ager , D. J. , Fleming , I. and Patei , S. K. 1981 . J. Chem. Soc., Perkins Trans. , 1 : 2527
   Google Scholar
• It has been reported that the reaction of 2-cyclohexen-1-one and (dimethylphenylsilyl)lithium gives 1,2-adduct in 62% yield; see Reference 4f
   Google Scholar
• Kingsbury , C. A. and Cram , D. J. 1960 . J. Am. Chem. Soc. , 82 : 1810
   Web of Science ®Google Scholar
• Sih , C. J. , Salomon , R. G. , Rice , P. , Sood , R. and Peruzzotti , G. 1975 . J. Am. Chem. Soc. , 97 : 857 L. Colommbo, C. Gennari, G. Resnati and C. Scolastico, J. Chem. Soc., Perkin Trans., 1, 1284 (1981); K. Tamao and N. Ishida, Tetrahedron Lett., 29, 4249 (1984); L. A. Paquette, J. Wright, G. J. Drtina and R. A. Roberts, J. Org. Chem., 92, 2960 (1987). Isobutylenol ether of 1,2-cyclohexanedione with lithium dimethylcuprate gives a 60:40 mixture of the cis and trans compounds, whereas the enol tosylate affords only trans isomer. J. A. Charonnat, A. L. Michelle and B. P. Keogh, Tetrahedron Lett., 31, 315 (1990)
   PubMed Web of Science ®Google Scholar
• Dauben , W. G. , Fonken , G. J. and Noyce , D. S. 1956 . J. Am. Chem. Soc. , 78 : 2579
   Web of Science ®Google Scholar
• Schleyer , P. V. R. 1967 . J. Am. Chem. Soc. , 89 : 699, 701
   Google Scholar
• McGarvey , G. J. and Williams , J. M. 1985 . J. Am. Chem. Soc. , 107 : 1435
   Google Scholar
• Tomioka , K. , Yasuda , K. , Kawasaki , H. and Koga , K. 1986 . Tetrahedron Lett. , 27 : 3247
   Google Scholar
• Reuter , J. M. , Sinha , A. and Salomon , R. G. 1978 . J. Org. Chem. , 83 : 2438
   Google Scholar
• Reich , H. J. , Renge , J. M. and Reich , I. L. 1975 . J. Am. Chem. Soc. , 97 : 5434 A. B. Smith and R. M. Scarborough, Jr., Tetrahedron Lett., 1649 (1978)
   Web of Science ®Google Scholar
• Kluge , A. F. , Untch , K. G. and Fried , J. F. 1972 . J. Am. Chem. Soc. , 94 : 7827
   PubMed Web of Science ®Google Scholar
• House , H. O. and Umen , M. J. 1973 . J. Org. Chem. , 38 : 3893
   Web of Science ®Google Scholar
• Corey , E. J. and Beames , D. J. 1972 . J. Am. Chem. Soc. , 94 : 7210 R. D. Stephens and C. E. Castro, J. Org. Chem., 28, 3313 (1963)
   Web of Science ®Google Scholar
• Hazato , A. , Tanaka , T. , Watanabe , K. , Bannai , K. , Toru , T. , Okamura , N. , Manabe , K. , Ohtsu , A. , Kamimoto , F. and Kurozumi , S. 1985 . Chem. Pharm. Bull. , 33 : 1815
   PubMedGoogle Scholar