Tosylmethylamines as "Nonstabilized" α-Aminocarbanion Synthon Equivalents: Advantages and Limitations

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6222-6225

  Katritzky, Alan R ^a   Feng, Daming ^a   Qi, Ming ^a  

^a University of Florida   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000093863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970733a     Document Type: Article

References (20)

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2. Transformations have been reported of phenyl and allyl sulfones, and of geminal bis-phenyl sulfones into the corresponding carbanions, see: Alonso, E.; Guijarro, D.; Yus, M. Tetrahedron 1995, 51, 2699. Clayden, J.; Julia, M. J. Chem. Soc., Chem. Commun. 1994, 2261. Chandrasekhar, S.; Yu, J.; Falck, J. R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
3. Transformations have been reported of phenyl and allyl sulfones, and of geminal bis-phenyl sulfones into the corresponding carbanions, see: Alonso, E.; Guijarro, D.; Yus, M. Tetrahedron 1995, 51, 2699. Clayden, J.; Julia, M. J. Chem. Soc., Chem. Commun. 1994, 2261. Chandrasekhar, S.; Yu, J.; Falck, J. R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
4. Transformations have been reported of phenyl and allyl sulfones, and of geminal bis-phenyl sulfones into the corresponding carbanions, see: Alonso, E.; Guijarro, D.; Yus, M. Tetrahedron 1995, 51, 2699. Clayden, J.; Julia, M. J. Chem. Soc., Chem. Commun. 1994, 2261. Chandrasekhar, S.; Yu, J.; Falck, J. R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5441.
5. After the present paper was written, Nájera and Yus groups reported transformation of α-aminomethyl sulfone into the α-nitrogenated organolithium compounds by using large excess of lithium and catalytic amount of naphthalene in moderate yields (25-54%, six examples), see Alonso, D. A.; Alonso, E.; Najera, C.; Ramón, D. J.; Yus, M. Tetrahedron 1997, 53, 4835.
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13. 2-promoted reactions have frequently been proposed to proceed by way of unstable organosamarium (III) intermediates, see ref 5. Walborsky, H. M.; Topolski, M. J. Org. Chem. 1992, 57, 370. Molander, G. A.; McKie, J. A. J. Org. Chem. 1991, 56, 4112.
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