Rhenium(VII) catalysis of prins cyclization reactions

Organic Letters

Volumn 10, Issue 21, 2008, Pages 4839-4842

  Tadpetch, Kwanruthai ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; RHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ISOMERISM;

ALDEHYDES; CATALYSIS; CYCLIZATION; ISOMERISM; MOLECULAR STRUCTURE; RHENIUM;

EID: 58149159597     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8019204     Document Type: Article

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38. This result stands in contrast to our Prins reaction approach to kendomycin, where an electron-rich aromatic ring led to side-chain exchange products as the major component in a TFA/DCM promoted reaction (ref 13).
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45. The "wet" reaction was run in water-saturated DCM. At 27°C, the concentration of water would be 0.137 M (0.186 wt %): Stephenson, R. M. J. Chem. Eng. Data 1992, 37, 80-95 With a catalyst concentration of 0.005 M, the molar ratio of water/Re(VII) would be ca, 27:1, For comparison, the molar ratio of commercial 70 wt % perrhenic acid is about 6:1 water/Re(VII). Presumably the difference in the water concentration led to the difference in outcome.
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