Stereospecific alkenylation of C-H bonds via reaction with β- heteroatom-functionalized trisubstituted vinyl triflones

Journal of the American Chemical Society

Volumn 119, Issue 18, 1997, Pages 4123-4129

  Xiang, Jason ^a   Jiang, Wanlong ^a   Gong, Jianchun ^a   Fuchs, P L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZOIC ACID; BROMINE; CYCLOHEXANE; FLUORINE; IODINE; PHTHALIMIDE; VINYL DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; HYDROGEN BOND; ISOMER; ISOMERISM; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0030950970     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963636s     Document Type: Article

References (24)

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13. For mechanistic studies and C-H functionalization reactions of alkynyl triflones, see: (a) Gona, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. Tetrahedron Lett. 1996, 37, 5269. (c) For aldehyde C-H functionalization reactions with alkynyl triflones, see: Gong, J.; Fuchs, P. L. Tetrahedron Lett. 1997, 38. 787.
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18. 2 moiety; a similar conformation experiment was not possible for (E)-11bI since both allylic methylene and methine were not sufficiently separated in chemical shift. (Matrix Presented)
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21. 2 moiety was irradiated. (Matrix Presented)
22. 14 who report a 47% yield for recrystallized material, prepared for securing an analytical sample. We find that the crude β-keto triflone may be routinely used for all synthetic purposes.
23. 2 moiety. Similar results were obtained from NOE phenyl irradiation experiments with the trisubstituted enol carbonates (Z)-26a and (E)-26a.
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