Design of chiral auxiliaries for the allene ether Nazarov cyclization

Journal of the American Chemical Society

Volumn 129, Issue 17, 2007, Pages 5328-5329

  Banaag, April R ^a   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

ALLENE DERIVATIVE;

ACIDITY; ARTICLE; CHIRALITY; CYCLIZATION; PREDICTION; PROTON TRANSPORT;

ALKADIENES; CYCLIZATION; DEOXYGLUCOSE; MODELS, CHEMICAL; MOLECULAR CONFORMATION;

EID: 34247898947     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja069342g     Document Type: Article

References (18)

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2. For reviews of the Nazarov reaction, see: (a) Harmata, M. Chemtracts 2004, 17, 416-435.
3. (b) Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577-7606.
4. (c) Pellissier, H. Tetrahedron 2005, 61, 6479-6517.
5. (d) Tius, M. A. Eur. J. Org. Chem. 2005, 2193-2206.
6. For recent examples of the Nazarov reaction, see: (a) Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544-9545.
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15. Our observations can also be rationalized by invoking a charge-dipole interaction between cation and pyranyl oxygen atom and the exo anomeric effect. We thank Professor William R. Roush for suggesting this.
16. Evidence suggests that this is the case. See: (a) Tius, M. A.; Busch-Petersen, J. Tetrahedron Lett. 1994, 35, 5181-5184.
17. (b) Yamada, H.; Tanigakiuchi, K.; Nagao, K.; Okajima, K.; Mukae, T. Tetrahedron Lett. 2004, 45, 5615-5618.
18. Lucero, C. G.; Woerpel, K. A. J. Org. Chem. 2006, 71, 2641-2647.