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Volumn 6, Issue 5, 2004, Pages 680-683

Polystyrene-supported phosphine-catalyzed aza-Baylis-Hillman reactions and the relationship between resin loading level and catalyst efficiency

Author keywords

[No Author keywords available]

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; IMINE; MONOMER; PHOSPHINE DERIVATIVE; POLYMER; POLYSTYRENE DERIVATIVE; REAGENT; RESIN; SCAVENGER; SOLVENT; SULFONAMIDE; TETRAHYDROFURAN;

EID: 4944256348     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049917a     Document Type: Article
Times cited : (61)

References (66)
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    • note
    • JandaJel is a registered trademark of the Aldrich Chemical Co. It is a polystyrene resin that is cross-linked by 1,4-bis-(4-vinylphenoxy)butane.
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    • For an examples of Baylis-Hillman reactions in which the substrates are polymer-supported, see: (a) Prien, O.; Rölfing, K.; Thiel, M.; Künzer, H. Synlett 1997, 325. (b) Richter, H.; Jung, G. Tetrahedron Lett. 1998, 39, 2729. (c) Richter, H.; Jung, G. Mol. Divers. 1998, 3, 191. (d) Kulkarni, B. A.; Ganesan, A. J. Comb. Chem. 1999, 1, 373. (e) Racker, R.; Doring, K.; Reiser, O. J. Org. Chem. 2000, 65, 6932.
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    • For an examples of Baylis-Hillman reactions in which the substrates are polymer-supported, see: (a) Prien, O.; Rölfing, K.; Thiel, M.; Künzer, H. Synlett 1997, 325. (b) Richter, H.; Jung, G. Tetrahedron Lett. 1998, 39, 2729. (c) Richter, H.; Jung, G. Mol. Divers. 1998, 3, 191. (d) Kulkarni, B. A.; Ganesan, A. J. Comb. Chem. 1999, 1, 373. (e) Racker, R.; Doring, K.; Reiser, O. J. Org. Chem. 2000, 65, 6932.
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    • For an examples of Baylis-Hillman reactions in which the substrates are polymer-supported, see: (a) Prien, O.; Rölfing, K.; Thiel, M.; Künzer, H. Synlett 1997, 325. (b) Richter, H.; Jung, G. Tetrahedron Lett. 1998, 39, 2729. (c) Richter, H.; Jung, G. Mol. Divers. 1998, 3, 191. (d) Kulkarni, B. A.; Ganesan, A. J. Comb. Chem. 1999, 1, 373. (e) Racker, R.; Doring, K.; Reiser, O. J. Org. Chem. 2000, 65, 6932.
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    • For an examples of Baylis-Hillman reactions in which the substrates are polymer-supported, see: (a) Prien, O.; Rölfing, K.; Thiel, M.; Künzer, H. Synlett 1997, 325. (b) Richter, H.; Jung, G. Tetrahedron Lett. 1998, 39, 2729. (c) Richter, H.; Jung, G. Mol. Divers. 1998, 3, 191. (d) Kulkarni, B. A.; Ganesan, A. J. Comb. Chem. 1999, 1, 373. (e) Racker, R.; Doring, K.; Reiser, O. J. Org. Chem. 2000, 65, 6932.
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    • note
    • Although DCM was a better solvent for 1b, it afforded a lower yield of 2a (Table 1, entry 1) than did THF (Table 1, entry 3) and, therefore, was not used in the subsequent experiments. This lower yield may have been due to the density of DCM and the propensity of 1b to stick to the flask wall above the reaction mixture.


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