A highly efficient carbon-carbon bond formation reaction via nucleophilic addition to N-alkylaldimines without acids or metallic species

Journal of the American Chemical Society

Volumn 127, Issue 42, 2005, Pages 14546-14547

  Nemoto, Hisao ^a   Kawamura, Tomoyuki ^a   Miyoshi, Norikazu ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; IMINE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; REACTION TIME; SYNTHESIS; TEMPERATURE;

ALDEHYDES; CARBON; IMINES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 27144469264     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054010h     Document Type: Article

References (27)

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5. A noteworthy exception has been reported; imines are more reactive than aldehydes in a palladium-tin-promoted system: Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647.
6. For recent examples of imines with postactivation, see: (a) Ishimaru, K.; Tsuru, K.; Yabuta, K.; Wada, M.; Yamamoto, Y.; Akiba, K.-Y. Tetrahedron 1996, 52, 13137-13144.
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20. For another one-pot reaction using H-MAC-TBS with aldehydes via migration of TBS group, see: (a) Nemoto, H.; Ma, R.; Suzuki, I.; Shibuya, M. Org. Lett. 2000, 2, 4245-4247.
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23. The MAC reagent 2 was not decomposed at room temperature for a few weeks. By way of precaution, we have usually stored 2 in a refrigerator, where 2 was not decomposed at all for more than a year. Preparation of 2: Nemoto, H.; Li, X.: Ma, R.; Suzuki, I.; Shibuya, M. Tetrahedron Lett. 2003, 44, 73-75.
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26. Presumably, the mild basic condition of this reaction is maintained by a slightly excess amount of imidazole (2.5 equiv), even if 2 (1.2 equiv) could be consumed to generate hydrogen cyanide (ca. 2.4 equiv).
27. Nucleophilic addition reaction to aldehydes with 10 was reported. Therefore, tertiary aniine can deprotonate 10 to produce the corresponding carbanion. Nemoto, H.; Kubota, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1994, 1665-1666.