Convergent cyclopentannelation process

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1681-1684

  Bee, Cisco ^a,b   Tius, Marcus A ^a,b  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF HAWAII CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CARBON; CYCLOPENTENE DERIVATIVE; CYCLOPENTANE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; CATALYSIS; CYCLIZATION;

CATALYSIS; CYCLIZATION; CYCLOPENTANES; INDICATORS AND REAGENTS;

EID: 0042229230     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034309+     Document Type: Article

References (23)

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5. (d) Schultz-Fademrecht, C.; Tius, M. A.; Grimme, S.; Wibbeling, B.; Hoppe, D. Angew. Chem., Int. Ed. 2002, 41, 1532-1535. For a review of the Nazarov reaction, see: Habermas, K. L.; Denmark, S.; Jones, T. K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1994; Vol. 45, pp 1-158.
6. For an overview of our work in this area, see: Tius, M. A. Acc. Chem. Res. 2003, in press, and references cited therein.
7. Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 916-924.
8. Tius, M. A.; Busch-Petersen, J.; Yamashita, M. Tetrahedron Lett. 1998, 39, 4219-4222.
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13. (d) Seyferth, D.; Langer, P.; Döring, M. Organometallics 1995, 14, 4457-4459. See also: Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L. J. Am. Chem. Soc. 1999, 121, 9769-9780.
14. Jang, W. B.; Hu, H.; Lieberman, M. M.; Morgan, J. A.; Stergiades, I. A.; Clark, D. S.; Tius, M. A. J. Comb. Chem. 2001, 3, 346-353.
15. 1H NMR chemical shift of the vinyl proton at C6. The vinyl proton of the (E)-isomers appears up to 1.2 ppm downfield of where it appears in the spectra of the (Z)-isomers. In cases in which a single isomer was isolated, stereochemistry was assigned by analogy, or, in the case of 9d and 12d, by NOE.
16. In the case of 9d, this hypothesis is supported by an MM2 calculation.
17. Tius, M. A.; Chu, C. C.; Nieves-Colberg, R. Tetrahedron Lett. 2001, 42, 2419-2422.
18. Dr. Oliver Weichold was the first person in our research group to prepare C6-substituted cyclopentenones through a variant of the process that is summarized in Scheme 2.
19. It is usually necessary to protect the α-amino function in this series to prevent polymerization of the products from occurring. In the case of 13, the polymerization through Michael addition to C6 by the amino function is sterically inhibited.
20. Harrington, P. E.; Murai, T.; Chu, C.; Tius, M. A. J. Am. Chem Soc. 2002, 124, 10091-10100.
21. 1H NMR spectrum because we were unable to resolve the enantiomers by chiral HPLC (Chiralcel OD column). To validate the Mosher method for our system, we measured the ee of (R)-9a by chiral HPLC (78%) and by Mosher's method (76%). (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519. (b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
22. 1H NMR spectrum because we were unable to resolve the enantiomers by chiral HPLC (Chiralcel OD column). To validate the Mosher method for our system, we measured the ee of (R)-9a by chiral HPLC (78%) and by Mosher's method (76%). (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519. (b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
23. Tius, M. A.; Gomez-Galeno, J.; Gu, X.-Q.; Zaidi, J. H. J. Am. Chem. Soc. 1991, 113, 5775-5783.