Application of radical chemistry to solid support synthesis

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5759-5762

  Berteina, Sabine ^a   De Mesmaeker, Alain ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

IODIDE; POLYSTYRENE; RADICAL; TRIBUTYLTIN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REDUCTION; SOLID STATE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032490966     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01172-1     Document Type: Article

References (11)

1. 1. P.H.H. Hermkens, H.C.J. Ottenheijm, D. Rees, Tetrahedron, 1996, 52, 4527-4554; P.H.H. Hermkens, H.C.J. Ottenheijm, D. Rees, Tetrahedron, 1997, 53, 5643-5678.
2. 1. P.H.H. Hermkens, H.C.J. Ottenheijm, D. Rees, Tetrahedron, 1996, 52, 4527-4554; P.H.H. Hermkens, H.C.J. Ottenheijm, D. Rees, Tetrahedron, 1997, 53, 5643-5678.
3. 2. a) A. Routledge, C. Abell, S. Balasubramanian, Synlett, 1997, 61-62.
4. b) X. Du, R.W. Armstrong, J. Org. Chem., 1997, 62, 5678-5679.
5. 3. Polystyrene beads, cross-linked with 1% divinyl benzene were used for all experiments.
6. 4. The compound 4 was synthesized by treatment with NaI and Chloramine T: T. Kometani, D. S. Watt, and T. Ji, Tetrahedron Lett., 1985, 26, 2043-2046.
7. 5. 2-tert-Butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine : commercially available by Fluka; R. Schwesinger, H. Schlemper, Angew. Chem., 1987, 99, 1212-1214.
8. 2 (6×4ml), diethyl ether (3×4ml) in order to eliminate the organotin compounds, then resin was dried under vacuum.
9. 7. Experimental procedure: 150-200 mg resin (0.1 mmol of loading substrate) was suspended in degassed benzene; then 10 eq. allyltributyltin and 0.5 eq. AIBN were added. The mixture was heated to reflux temperature under an argon atmosphere. After 5 additions of 1 eq. allyltributyltin and 0.2 eq. AIBN, (46h), the resin was washed as above.
10. 8. S. Berteina, S. Wendeborn, W. K.-D. Brill, A. De Mesmaeker. Synlett in Press; for a very recent example of radical allylation reaction on solid support see: M.P. Sibi, S.V. Chandramouli, Tetrahedron Lett., 1997, 38, 8929-8932.
11. 8. S. Berteina, S. Wendeborn, W. K.-D. Brill, A. De Mesmaeker. Synlett in Press; for a very recent example of radical allylation reaction on solid support see: M.P. Sibi, S.V. Chandramouli, Tetrahedron Lett., 1997, 38, 8929-8932.