Chemoselective Reduction of Saturated Aldehydes and Ketones over Unsaturated Carbonyls with Bowl-shaped Tris(2,6-diphenylbenzyl)tin Hydride

Abstract

A high chemoselective reduction of saturated aldehydes and ketones in the presence of unsaturated carbonyls (aromatic and α,β-unsaturated carbonyls) has been realized by using the structurally unique, bowl-shaped tris(2,6-diphenylbenzyl)tin hydride (TDTH) under the influence of Me₂AlCl or BF₃·OEt₂ as Lewis acids.

Key words

chemoselective reduction - aldehyde - ketone - tin - Lewis acid

References

• 1 Sasaki K. Kondo Y. Maruoka K. Angew. Chem. Int. Ed.  2001,  40:  411 
• For related study on the similar bowl-shaped tris(2,6-diphenylbenzyl)silyl moiety and tris(2,6-diphenylbenzyl)amine, see:
• 2a Iwasaki A. Kondo Y. Maruoka K. J. Am. Chem. Soc.  2000,  122:  10238 
• 2b Naiki M. Shirakawa S. Kon-i K. Kondo Y. Maruoka K. Tetrahedron Lett.  2001,  42:  5467 
• Recent chemoselective reactions between two different aldehydes:
• 3a Maruoka K. Saito S. Yamamoto H. Synlett  1994,  439 
• 3b Marx A. Yamamoto H. Angew. Chem. Int. Ed.  2000,  39:  178 
• 3c Asao N. Asano T. Ohishi T. Yamamoto Y. J. Am. Chem. Soc.  2000,  122:  4817 
• 3d Asao N. Shimada T. Yamamoto Y. Tetrahedron Lett.  2000,  41:  9533 
• 3e Mori A. Ohno H. Inoue S. Chem. Lett.  1992,  631 
• Chemoselective reductions between aldehydes and ketones:
• 4a Yoon NM. Park KB. Gyoung YS. Tetrahedron Lett.  1983,  24:  5367 
• 4b Kim S. Kang HJ. Yang S. Tetrahedron Lett.  1984,  25:  2985 
• 4c Cha JS. Kim EJ. Kwon OO. Kim JM. Synlett  1995,  331 
• Recent chemoselective reductions between two different ketones:
• 5a Gemal AL. Luche J.-L. J. Org. Chem.  1979,  44:  4187 
• 5b Ward DE. Rhee CK. Zoghaib WM. Tetrahedron Lett.  1988,  29:  517 
• 5c Ito H. Yamanaka H. Ishizuka T. Tateiwa J. Hosomi A. Synlett  2000,  479 
• 6 Brown HC. Krishnamurthy S. J. Am. Chem. Soc.  1972,  94:  7159