Mannich-type reaction catalyzed by dicyanoketene ethylene acetal and the related polymer-supported π-acid: Aldimine-selective reactions in the coexistence of aldehydes

Synlett

Volumn , Issue 3, 2000, Pages 406-408

  Tanaka, Nobuyuki ^a   Masaki, Yukio ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Aldimine selectivity; Enolsilyl ethers; Mannich type reaction; Polymeric acid catalyst; Recyclable catalyst

Indexed keywords

ACETAL; ALDEHYDE; IMINE; KETENE DERIVATIVE; SILANE DERIVATIVE; SOLVENT; TETRACYANOETHYLENE;

ACETYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 0034007917     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (13)

1. Reviews: Akelah, A.; Sherrington, D. C. Chem. Rev 1981, 81, 557. Fréchet, J. M. J. Tetrahedron 1981, 37, 663. Shuttleworth, S. J.; Allin,S. M.; Sharma, P. K. Synthesis 1997, 1217.
2. Reviews: Akelah, A.; Sherrington, D. C. Chem. Rev 1981, 81, 557. Fréchet, J. M. J. Tetrahedron 1981, 37, 663. Shuttleworth, S. J.; Allin,S. M.; Sharma, P. K. Synthesis 1997, 1217.
3. Reviews: Akelah, A.; Sherrington, D. C. Chem. Rev 1981, 81, 557. Fréchet, J. M. J. Tetrahedron 1981, 37, 663. Shuttleworth, S. J.; Allin,S. M.; Sharma, P. K. Synthesis 1997, 1217.
4. Kobayashi, S.; Nagayama, S. Synlett 1997, 653 and references cited therein.
5. a) Masaki, Y.; Miura, T.; Ochiai, M. Bull. Chem. Soc. Jpn. 1996, 69, 195.
6. b) Masaki, Y.; Miura, T. Synth. Commun. 1995, 25, 1981.
7. c) Masaki, Y.; Miura, T. Tetrahedron 1995, 57, 10477.
8. The polymer is estimated to contain the dicyanoketene acetal moiety 2.74 mmol/g (polymer) from elemental analysis.
9. Masaki, Y.; Tanaka, N.; Miura, T. Tetrahedron Lett. 1998, 39, 5799. Tanaka, N.; Masaki, Y. Synlett 1999, 1277.
10. Masaki, Y.; Tanaka, N.; Miura, T. Tetrahedron Lett. 1998, 39, 5799. Tanaka, N.; Masaki, Y. Synlett 1999, 1277.
11. Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1997, 119, 10049 and references cited therein.
12. Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641.
13. Akiyama, T.; Takaya, J.; Kagoshima, H. Chem. Lett. 1999, 947.