Mannich reactions of resin-bound substrates: 2. A versatile three- component solid-phase organic synthesis methodology

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 967-970

  McNally, James J ^a   Youngman, Mark A ^a   Dax, Scott L ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; AMINE; BENZALDEHYDE; COPPER ION; FUNCTIONAL GROUP; PARAFORMALDEHYDE; PIPERAZINE DERIVATIVE; RESIN; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0032567888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10716-X     Document Type: Article

References (11)

1. 1. Armstrong, R. W. Patent WO 95/02566, 1995.
2. 2. Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819-7822.
3. 3. Tramontini, M.; Angiolini, L. Mannich Bases: Chemistry and Uses, CRC Press Inc, Boca Raton, FL 1994.
4. 4. Kobayashi, S.; Moriwaki, M.; Akiyama, R.; Suzuki, S.; Hachiya, I. Tetrahedron Lett. 1996, 37, 7783-7786.
5. 5. For example, see Cook, S. C.; Dax, S. L. Biooorg. Med. Chem. Lett. 1996, 6, 797-802.
6. 6. Youngman, M. A.; Dax, S. L. Tetrahedron Lett. 1997, 38, 6347-6350.
7. 7. The resin was washed: 3 × 3mL DMF, 3 × 3mL MeOH, 3 × 3mL THF, 3 × 3mL DCM.
8. 8. Hoekstra,W. J.; Greco, M. N.; Yabut, S. C.; Hulshizer, B. L.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2629-2632.
9. 4OH then 1 × 3mL DMF), 3 × 3mL MeOH, 3 × 3mL THF, 3 × 3mL DCM.
10. 3OD for fixed frequency lock and chemical shift; HPLC were obtained on a Hewlett Packard HP1050 using a gradient (10:90 to 90:10) of acetonitrile/water with 0.1% trifluoroacetic acid as eluent and UV detection at either 217 nM or 220 nM; Mass spectra were obtained on a Micromass Platform II using electrospray ionization and probe = 4.0 kV or on a Hewlett Packard HP5989 MS Engine using particle beam chemical ionization with ammonia as reagent gas.
11. 11. Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789-3792.