Diastereoselective [4 + 4]-photocycloaddition reactions of pyran-2-ones: Rapid access to functionalized 5-8-5 skeletons

Organic Letters

Volumn 8, Issue 18, 2006, Pages 4075-4078

  Song, Dong ^a   McDonald, Robert ^a   West, F G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748923121     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061576h     Document Type: Article

References (37)

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27. The fusicoccane/cotylen numbering system is used. See Scheme 1.
28. Endo and exo in this context refer to the relative orientations of the two diene reactants in the [4 + 4]-cycloaddition transition state. The endo transition state places the furan C-3 and C-4 over the internal carbons of the pyran-2-one diene system, leading to a product in which the lactone and ether bridges are cis in the newly formed cyclooctadiene. The exo transition state places the furan C-3 and C-4 over the lactone moiety, leading to a product with the lactone and ether bridges trans disposed on the cyclooctadiene. For substrates such as 1 possessing a preexisting stereocenter, two endo and two exo products are possible, corresponding to approach of the furan from the same or the opposite face as the OR group.
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33. The corresponding TBS and MOM ethers also failed to react with malonyl dichloride. Thus, although sterics may play a role, we believe that inductive deactivation of the silyl enol ether is the principal reason for the negative outcome of this annulation.
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35. We anticipated removal of the triflate could take place either before or after photocycloaddition. The latter approach would rely on our previous observation that hydrogenolysis of vinyl inflates in [4 + 4]-cycloadducts of 4-trifloxypyran-2-ones occurs efficiently under conditions for hydrogenation of the cyclooctadiene (see ref 8b).
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37. X-ray data in CIF format can be found in the Supporting Information.