Ruthenium catalyzed ring rearrangement: A rapid entry to substituted aza- and oxacycles

Tetrahedron

Volumn 58, Issue 37, 2002, Pages 7503-7518

  Ovaa, Huib ^a   Stapper, Christian ^b   Van Der Marel, Gijs A ^a   Overkleeft, Hermen S ^a   Van Boom, Jacques H ^a   Blechert, Siegfried ^b  

^a LEIDEN UNIVERSITY   (Netherlands)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Asymmetric synthesis; Heterocycles; Rearrangement; Ruthenium

Indexed keywords

AMINE; ETHER DERIVATIVE; FURAN DERIVATIVE; OXEPINE DERIVATIVE; PYRAN DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; DIMERIZATION; METHODOLOGY; MOLECULE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037048460     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00832-3     Document Type: Article

References (22)

1. For recent reviews see: (a) Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18 (b) Fürstner A. Angew. Chem. Int. Ed. Engl. 39:2000;3013 (c) Blechert S. Pure Appl. Chem. 71:(8):1999;1393.
2. For recent reviews see: (a) Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18 (b) Fürstner A. Angew. Chem. Int. Ed. Engl. 39:2000;3013 (c) Blechert S. Pure Appl. Chem. 71:(8):1999;1393.
3. For recent reviews see: (a) Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18 (b) Fürstner A. Angew. Chem. Int. Ed. Engl. 39:2000;3013 (c) Blechert S. Pure Appl. Chem. 71:(8):1999;1393.
4. (a) Ovaa H., Stragies R., van der Marel G.A., van Boom J.H., Blechert S. Chem. Commun. 2000;1501
5. (b) Voigtmann U., Blechert S. Org. Lett. 2:2000;3971
6. (c) Voigtmann U., Blechert S. Synthesis. 6:2000;893
7. (d) Stragies R., Blechert S. J. Am. Chem. Soc. 122:2000;9584
8. (e) Buschmann N., Rückert A., Blechert S. J. Org. Chem. 67:2002;4325.
9. Adams J.A., Gair-Ford J., Stamatos P.J., Hoveyda A.H. J. Org. Chem. 64:1999;9690.
10. Ovaa H., Codee J.D.C., Lastdrager B., Overkleeft H.S., van der Marel G.A., van Boom J.H. Tetrahedron Lett. 39:1998;7987.
11. . For a review on asymmetric transition metal catalyzed allylic alkylations see: Trost B.M., van Vranken D.L. Chem. Rev. 96:1996;395.
12. 3, DMF. (ii) TsCl, pyridine) in order to facilitate separation of the enantiomers on a Chiralcel OD Gold column (0.5% iPrOH in hexane, 0.9 mL/min, 218 nm).
13. Stragies R., Blechert S. Tetrahedron. 55:1999;8179.
14. (a) Rutjes F.P.J.T., Kooistra T.M., Hiemstra H., Schoemaker H.E. Synlett. 1998;192
15. (b) Ovaa H., Leeuwenburgh M.A., van der Marel G.A., van Boom J.H. Tetrahedron Lett. 39:1998;3025.
16. 3N) during work-up and purification by column chromatography in order to prevent this elimination reaction.
17. Johnson C.R., Golebiowski A., Steensma D.H. J. Am. Chem. Soc. 114:1992;9414.
18. Stragies R., Blechert S. J. Am. Chem. Soc. 122:2000;9584.
19. . For the deprotection protocol see: Fukuyama T., Joe C.-K., Cheung M. Tetrahedron Lett. 52:1995;1922.
20. Zuercher W.J., Hashimoto M., Grubbs R.H. J. Am. Chem. Soc. 118:1996;6634.
21. Wessel H.-P., Iversen T., Bundle D.R. J. Chem. Soc., Perkin Trans. 1. 1985;2247.
22. Instead of working in a glove box, Schlenk technique may also be used. Solid Grubbs catalyst [Ru] can be handled in air.