Synthesis of highly functionalized azabicycles via 2-alkenyl sulfoximines

Synthesis

Volumn , Issue 13, 2006, Pages 2224-2232

  Reggelin, Michael ^a   Kühl, Jochen ^a   Kaiser, Jan Philipp ^a   Bühle, Philipp ^b  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b MERCK KGAA   (Germany)

Author keywords

Amino aldehydes; Asymmetric synthesis; Bicyclic compounds; Metallation; Sulfoximines

Indexed keywords

ALDEHYDES; ALKYLATION; GAMMA RAYS; HYDROXYLATION; KETONES; POLYPEPTIDES; SYNTHESIS (CHEMICAL);

AMINO ALDEHYDES; ASYMMETRIC SYNTHESIS; BICYCLIC COMPOUNDS; METALLATION; SULFOXIMINES;

AROMATIC COMPOUNDS;

2 ALKENYL SULFOXIMINE DERIVATIVE; ALDEHYDE DERIVATIVE; ALKANONE; AZABICYCLE DERIVATIVE; BENZO 7,12 DIOXASPIRO[5.6]DODECAN 3 ONE; HETEROCYCLIC COMPOUND; HYDRAZINE; IMINE; N (1 HYDROXYMETHYL 2 METHYLPROPYL) 4 HYDROXY 8A (TOLYLSULFONIMIDOYLMETHYL)OCTAHYDROQUINOLIN 6 ONE; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 1 BENZYL 3 (TOLYLSULFONIMIDOYLMETHYL) 2,5 DIHYDRO 1H PYRROLE; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 2 [3 HYDROXY 3 [8 [1 (TOLYLSULFONIMIDOYL)METHYLIDENE] 1,4 DIOXASPIRO[4.5]DEC 7 YL]PROPYL]ISOINDOLE 1,3 DIONE; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 2,5 DIBENZYL 6A (TOLYLSULFONIMIDOYLMETHYL)OCTAHYDROPYRROLO[3,4 B]PYRROL 3 OL; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 3 (TOLYLSULFONIMIDOYLMETHYL)BENZO 7,12 DIOXASPIRO[5.6]DODEC 2 ENE; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 4 (TOLYLSULFONIMIDOYLMETHYL) 3,6 DIHYDRO 2H PYRIDINE 1 CARBOXYLIC ACID TERT BUTYL ESTER; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 4 HYDROXY 8A (TOLYLSULFONIMIDOYLMETHYL)OCTAHYDRO[1,6]NAPHTHYRIDINE 6 CARBOXYLIC ACID TERT BUTYL ESTER; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 4 HYDROXY 8A (TOLYLSULFONIMIDOYLMETHYL)OCTAHYDROQUINOLIN 6 ONE ETHYLENE KETAL; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 4 HYDROXY 8A (TOLYLSULFONIMIDOYLMETHYL)OCTAHYDROQUINOLIN 6 ONE XYLYLKETAL; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 5 BENZYL 2 TERT BUTOXYMETHYL 6A (TOLYLSULFONIMIDOYLMETHYL)OCTAHYDROPYRROLO[3,4 B]PYRROL 3 OL; N [1 [TERT BUTYL(DIMETHYL)SILANYLOXYMETHYL] 2 METHYLPROPYL] 8 (TOLYLSULFONIMIDOYLMETHYL) 1,4 DIOXASPIRO[4.5]DEC 7 ENE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROXYLATION; STEREOCHEMISTRY;

EID: 33746078804     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942427     Document Type: Article

References (17)

1. Reggelin, M.; Junker, B.; Heinrich, T.; Slavik, S.; Bühle, P. J. Am. Chem. Soc. 2006, 128, 4023.
2. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467.
3. Reggelin, M.; Zur, C. Synthesis 2000, 1.
4. Reggelin, M.; Weinberger, H.; Gerlach, M.; Welcker, R. J. Am. Chem. Soc. 1996, 118, 4765.
5. Reggelin, M.; Weinberger, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 444.
6. Reggelin, M.; Weinberger, H. Tetrahedron Lett. 1992, 33, 6959.
7. Reggelin, M.; Welcker, R. Tetrahedron Lett. 1995, 36, 5885.
8. Reggelin, M.; Junker, B. Chem.-Eur. J. 2001, 7, 1232.
9. Reggelin, M.; Weinberger, H.; Heinrich, T. Liebigs Ann. Red. 1997, 1881.
10. Reggelin, M.; Gerlach, M.; Vogt, M. Eur. J. Org. Chem. 1999, 1011.
11. Reggelin, M.; Heinrich, T.; Junker, B.; Antel, J.; Preuschoff, U. Solvay Pharmaceuticals GmbH, Germany Application WO 99/58500, 72, 1999.
12. Reggelin, M.; Heinrich, T. Angew. Chem. Int. Ed. 1998, 37, 2883.
13. Bund, J.; Gais, H. J.; Erdelmeier, I. J. Am. Chem. Soc. 1991, 113, 1442.
14. Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1989, 30, 4165.
15. Babler, J. H.; Spina, K. P. Synth. Commun. 1984, 14, 39.
16. N2′ reactions of 2-alkenyl sulfoximines with C-nucleophiles, see: Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453.
17. Rich, D. H.; Ripka, A. S. Curr. Opin. Chem. Biol. 1998, 2, 441.