Carbon-carbon bond formation via the Mitsunobu reaction on solid supports

Tetrahedron Letters

Volumn 40, Issue 47, 1999, Pages 8205-8209

  Chaturvedi, Surendrakumar ^a   Otteson, Ken ^a   Bergot, John ^a  

^a APPLIED BIOSYSTEMS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKYL GROUP; AMIDE; PHOSPHINE DERIVATIVE; POLYMER;

ALKYLATION; ARTICLE; SOLID;

EID: 0033584987     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01705-0     Document Type: Article

References (18)

1. Richter, L. S.; Gadeck, T. R. Tetrahedron Lett. 1994, 35, 4705-4706.
2. Rano, T. A.; Chapman, T. K. Tetrahedron Lett. 1995, 36, 3789-3792.
3. Krchnak, V.; Flegelova, Z.; Weichsel, A. S.; Lebl, M. Tetrahedron Lett. 1995, 36, 6193-6196.
4. Macor, J. E.; Wehner, J. M. Tetrahedron Lett. 1991, 32, 7195-7198.
5. Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; Ito, S. Tetrahedron Lett. 1995, 36, 2531-2534 and references cited therein.
6. Dankwardt, S. T.; David, S. B.; John Jr., A.; Cindy, H. Synlett 1997, 854-856.
7. Hamper, B. C.; Dukesherer, D. R.; South, M. S. Tetrahedron Lett. 1996, 37, 3671-3674.
8. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 30, 8135-8173.
9. Balkenhohl, F.; Bussche-Hunnefeld, C. V.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288-2337.
10. Marzinzik, A. L.; Felder, E. R. Tetrahedron Lett. 1996, 37, 1003-1006.
11. Watson, S. P.; Wilson, R. D.; Judd, D. B.; Richards, S. A. Tetrahedron Lett. 1997, 38, 9065-9068.
12. Marzinzik, A. L.; Felder, E. R. Tetrahedron Lett. 1996, 37, 1003-1006.
13. The syntheses were performed in a parallel array on a robotic liquid handler synthesizer (SOLARIS™). The additions, aspirations, and washings were performed using a robotic arm possessing four alternate aspirating and coaxial tips. The 4-(2′,4′-dimethoxyphenylfluorenylmethoxycarbonylaminomethyl)phenoxy polystyrene, 'Rink Amide resin', loaded at 0.6 mmol Fmoc-amine/gm was placed in a round bottomed flask and was subjected to Fmoc cleavage with 20% piperidine in DMF for 10 min. The resin was subjected to a series of washings (3x5 mL) with DMF, MeOH, and DCM. Subsequently, the next step was coupling of the HMBA to the resin using 3 equivalents of DIC, HOBt, and HMBA in DMA for 4 h. At this stage, the solvent was drained and each flask was subjected to standard washing cycles. The next step was the Mitsunobu C-C alkylation using fivefold excess of tributylphosphine, N,N,N′,N′ -tetramethylazodicarboxamide, and the active methylene compounds was conducted in dry THF at room temperature. After shaking the mixture for 12 h at room temperature, the reagents were drained and the resin was subjected to the washing cycles. Cleavage of products from the resin was performed with 20% TFA in DCM over 45 min at rt gave the desired compounds.
14. Structure of dimeric ester and the resultant Mitsunobu product product: (equation presented)
15. Crowley, J. I.; Harvey, T. B.; Rapoport, H. J. Macromol. Sci. Chem. 1973, A7(5), 1117-1126.
16. Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans, 1 1982, 2319.
17. Hodge, P. Chem. Rev. 1997, 26, 417-424.
18. Yan, B.; Sun, Q. J. Org. Chem. 1998, 63, 55-58 and references cited therein.