Enantiospecific Synthesis of 9,10-Dihalocamphors

Synlett

Volumn , Issue 1, 2004, Pages 134-136

  García Martínez, Antonio ^a   Teso Vilar, Enrique ^b   García Fraile, Amelia ^b   Moya De La Cerero, Santiago ^a   Díaz Morillo, Cristina ^b   Pérez Morillo, Rocío ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

Bicyclic compounds; Chirality; Electrophilic additions; Halides; Ketones

Indexed keywords

CAMPHOR DERIVATIVE;

ADDITION REACTION; ARTICLE; CHIRALITY; ENANTIOMER; SYNTHESIS; WAGNER MEERWEIN REARRANGEMENT;

EID: 0347601777     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43347     Document Type: Article

References (25)

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6. An interesting review on the preparation of camphor derivatives is: Money, T. Nat. Prod. Rep. 1985, 253.
7. 2) see: (a) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203. (b) Paquette, L. A.; Wang, H.-L.; Su, Z.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5213. (c) About catalyst 4 and other related derivatives see: García Martînez, A.; Teso Vilar, E.; García Fraile, A.; de la Moya Cerero, S.; Lora Maroto, B. Tetrahedron: Asymmetry 2003, 14, 1959; and references therein.
8. 2) see: (a) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203. (b) Paquette, L. A.; Wang, H.-L.; Su, Z.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5213. (c) About catalyst 4 and other related derivatives see: García Martînez, A.; Teso Vilar, E.; García Fraile, A.; de la Moya Cerero, S.; Lora Maroto, B. Tetrahedron: Asymmetry 2003, 14, 1959; and references therein.
9. 2) see: (a) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203. (b) Paquette, L. A.; Wang, H.-L.; Su, Z.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5213. (c) About catalyst 4 and other related derivatives see: García Martînez, A.; Teso Vilar, E.; García Fraile, A.; de la Moya Cerero, S.; Lora Maroto, B. Tetrahedron: Asymmetry 2003, 14, 1959; and references therein.
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21. For a review see: de la Moya Cerero, S.; García Martínez, A.; Teso Vilar, E.; García Fraile, A.; Lora Maroto, B. J. Org. Chem. 2003, 68, 1451.
22. 2) produces the selective removal of the C(3)-bromine, giving place to pure 1(Br/H) in 95% yield.
23. 13C NMR, IR and MS agree with the structure.
24. 13C NMR, IR and MS agree with the structure.
25. 14BrIO: 355.9273. Found: 355.9269.