Enantioselective Claisen rearrangement of difluorovinyl allyl ethers

Chemical Communications

Volumn , Issue 22, 1998, Pages 2441-2442

  Ito, Hisanaka ^a   Sato, Azusa ^a   Kobayashi, Tetsuo ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BORON; ETHER DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER;

EID: 0032556518     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807157h     Document Type: Article

References (21)

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18. 3 at 26°C. 3a: 41.1; 3b: 18.6; 3c: -18.3; 3d: -8.8; 3e: -20.3.
19. In the absence of Lewis acid, the E isomer 2b smoothly rearranged to 3b even at room temperature, possibly due to the presence of the phenolic hydroxy group, to form an intramolecular hydrogen bond between the ethereal oxygen.
20. The relative stereochemistry of compound 6 was determined via conversions to 10 and a NOESY experiment, as shown in Scheme 4.
21. 1H NMR analysis of the crude mixture, we were unable to find a clean method for cleavage of the hydroxyphenyl moiety.