New and Efficient Synthesis of Stannyl Enamines

Abstract

α- and β-stannyl enamines have been synthesized in fairly to excellent yields starting from N-benzyl, N-tosyl ynamine and various organotin reagents under standard palladium catalysis.

Key words

tin - hydrostannation - stannyl enamines - palladium

References

• 1 Pereyre M. Quintard J.-P. Rahm A. Tin in Organic Synthesis   Butterworths & Co. Ltd Publ.; London: 1986. 
• 2 Farina V. Krishnamurthy V. Scott WJ. The Stille Reaction   John Wiley and sons Inc.; New York: 1998. 
• 3a Chandra G. George TA. Lappert MF. Chem. Commun.  1967,  116 
• 3b George TA. Lappert MF. J. Organomet. Chem.  1968,  14:  327 
• 3c Kazankova MA. Zverkova TI. Levin MZ. Lutsenko IF. J. Gen. Chem. USSR  1975,  45:  66 
• 3d Bogoradovskii ET. Liepins E. Russ. J. Gen. Chem.  1994,  64:  1102  and references therein
• 4 Murch P. Williamson BL. Stang PJ. Synthesis  1994,  1255 
• 5 Witulski B. Stengel T. Angew. Chem., Int. Ed. Engl.  1998,  37:  489 
• 6 Witulski B. Buschmann N. Bergstrasser U. Tetrahedron  2000,  56:  8473 
• 7 Zhang HX. Guibe F. Balavoine G. J. Org. Chem.  1990,  55:  1857 
• 8 Quayle P. Wang J. Xu J. Urch CJ. Tetrahedron Lett.  1998,  39:  481 
• 9 Mitchell TN. Amamria A. Killing H. Rutschow D. J. Organomet. Chem.  1986,  304:  257