Synthesis and Diastereoselective Reactions of N,N-Dibenzylamino Aldehydes and Related Compounds

Chemical Reviews

Volumn 99, Issue 5, 1999, Pages 1121-1162

  Reetz, Manfred T ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000763561     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr980417b     Document Type: Article

References (336)

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154. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
155. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
156. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
157. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
158. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
159. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
160. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
161. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
162. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
163. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
164. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431-432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
165. Alternative theoretical models for these and/or related stereoselective reactions: (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552. (b) Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916-1917. (c) Kumar, V. A.; Venkatesan, K.; Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Metha, G. Tetrahedron Lett. 1992, 33, 3069-3072. (d) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210. (e) Metha, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140-6142. (f) Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. (g) Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem. 1992, 104, 1087-1089; Angew. Chem., Int. Ed. Engl. 1992, 31, 1019. (h) Wu, Y.-D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018-5027. (i) Wu, Y.-D.; Houk, K. N.; Florez, J.; Trost, B. M. J. Org. Chem. 1991, 56, 3656-3664. (j) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-9018. (k) Senju, T.; Tomoda, S. Chem. Lett. 1997, 431- 432. (l) Atkinson, R. S. Stereoselective Synthesis; Wiley: New York, 1995.
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