A chiral pool approach to the synthesis of optically active tetrahalo norbornyl building blocks

Organic Letters

Volumn 10, Issue 14, 2008, Pages 3029-3032

  Khan, Faiz Ahmed ^a   Sudheer, Ch ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

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Indexed keywords

EID: 59949105096     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800990m     Document Type: Article

References (29)

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7. For selected list of reports on the applications of norbornyl derivatives from our group, see: (a) Khan, F. A.; Rout, B. J. Org. Chem. 2007, 72, 7011.
8. (b) Khan, F. A.; Rout, B. Tetrahedron Lett. 2006, 47, 5251.
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13. (g) Khan, F. A.; Satapathy, R.; Dash, J.; Savitha, G. J. Org. Chem. 2004, 69, 5295.
14. (h) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
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18. Mamedov, E. G. Russ. J. Org. Chem. 2002, 38, 15. In this report, the Diels-Alder adduct of 1a and (-)-menthyl acrylate was transformed to 7 without specifying if a single diastereomer was formed. Even the authentic 7 obtained by repeated crystallization of acrylic acid adduct with (-)-ephedrine, assumed to be optically pure, appears to have an ee of 66%. We came to this conclusion by comparing the specific rotation values obtained by us and Mamedov. We confirmed the enantiopurity of 7 obtained by our method using chiral HPLC.
19. Khan, F. A.; Upadhyaya, S. K. Unpublished results.
20. For selected examples, see references cited in ref 5h.
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24. 10c proposed steric and electronic factors play a crucial role.
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29. Dienes 1a,b and and dienophiles 2, 10, 18, and 25 are prepared from cyclopentadiene and d-mannitol, respectively.