Microwave-assisted synthesis of allylic amines: Considerable rate acceleration in the hydrozirconation-transmetalation-aldimine addition sequence

Organic and Biomolecular Chemistry

Volumn 2, Issue 4, 2004, Pages 443-445

  Wipf, Peter ^a   Janjic, Jelena ^a   Stephenson, Corey R J ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; COMPLEXATION; MICROWAVES; MIXTURES; ORGANOMETALLICS; PRESSURE EFFECTS; RATE CONSTANTS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; TOLUENE;

ALLYLIC AMINES; MICROWAVE-ASSISTED SYNTHESIS;

AMINES;

ALLYL COMPOUND; AMINE; HYDROGEN; IMINE; SILICATE; ZIRCONIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; SYNTHESIS;

ALLYL COMPOUNDS; AMINES; HYDROGEN; IMINES; MICROWAVES; MOLECULAR STRUCTURE; SILICATES; ZIRCONIUM;

EID: 1342302534     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b316741k     Document Type: Article

References (24)

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12. For representative additions to aldehydes, see: P. Wipf, N. Jayasuriya and S. Ribe, Chirality, 2003, 15, 208. Ketones: P. Wipf and C. R. J. Stephenson, Org. Lett., 2003, 5, 2449. Enones: P. Wipf and J. H. Smitrovieh, J. Org. Chem., 1991, 56, 6494. Epoxides: P. Wipf and W. Xu, J. Org. Chem., 1993, 58, 825. Esters: P. Wipf and W. Xu, J. Org. Chem., 1993, 58, 5880. Isocyanates: E. Negishi, D. R. Swanson and S. R. Miller, Tetrahedron Lett., 1988, 29, 1631. Nitrones: S. U. Pandya, C. Garçon, P. Y. Chavant, S. Py and Y. Vallée, Chem. Commun., 2001, 1806.
13. For representative additions to aldehydes, see: P. Wipf, N. Jayasuriya and S. Ribe, Chirality, 2003, 15, 208. Ketones: P. Wipf and C. R. J. Stephenson, Org. Lett., 2003, 5, 2449. Enones: P. Wipf and J. H. Smitrovieh, J. Org. Chem., 1991, 56, 6494. Epoxides: P. Wipf and W. Xu, J. Org. Chem., 1993, 58, 825. Esters: P. Wipf and W. Xu, J. Org. Chem., 1993, 58, 5880. Isocyanates: E. Negishi, D. R. Swanson and S. R. Miller, Tetrahedron Lett., 1988, 29, 1631. Nitrones: S. U. Pandya, C. Garçon, P. Y. Chavant, S. Py and Y. Vallée, Chem. Commun., 2001, 1806.
14. For representative additions to aldehydes, see: P. Wipf, N. Jayasuriya and S. Ribe, Chirality, 2003, 15, 208. Ketones: P. Wipf and C. R. J. Stephenson, Org. Lett., 2003, 5, 2449. Enones: P. Wipf and J. H. Smitrovieh, J. Org. Chem., 1991, 56, 6494. Epoxides: P. Wipf and W. Xu, J. Org. Chem., 1993, 58, 825. Esters: P. Wipf and W. Xu, J. Org. Chem., 1993, 58, 5880. Isocyanates: E. Negishi, D. R. Swanson and S. R. Miller, Tetrahedron Lett., 1988, 29, 1631. Nitrones: S. U. Pandya, C. Garçon, P. Y. Chavant, S. Py and Y. Vallée, Chem. Commun., 2001, 1806.
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22. A CEM Discover single mode microwave reactor with controlled temperature, power, pressure and time settings was used for all reactions.
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24. Flash heating is accomplished by continuous irradiation at high (100-150) wattage until the target temperature is reached in the reaction vessel. On the CEM Discover reactor, this is accomplished using the "powertime" setting.