Intramolecular Reaction of (γ-Alkoxyallyl)stannane with Aldehyde: Origin of the Stereoselectivities

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7439-7446

  Kadota, Isao ^a   Kawada, Miho ^a   Gevorgyan, Vladimir ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001233496     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971309c     Document Type: Article

References (34)

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29. 1-NMR, and elemental analyses or high-resolution mass spectra. Because of their low stability, the aldehydes 14-17 could not be fully characterized. See the Experimental Section.
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33. To comfirm the stereochemical assignment, the cis isomer 40 was converted to a bicyclic lactone by four steps in good yield. In contrast, the trans isomer 39 did not give any cyclized product under the same conditions because of the steric problem of the trans-fused 5-5 ring system.
34. 4, the reaction via 51 and 52 may be involved to a certain extent.