A novel tandem [4++2] cycloaddition-elimination reaction of 4,4- dimethyl-2-styryl-1,3-oxathianes with olefins

Tetrahedron Letters

Volumn 41, Issue 3, 2000, Pages 371-375

  Nishide, Kiyoharu ^a   Ohsugi, Shin Ichi ^a   Node, Manabu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Oxathianes; Tandem 4++2 cycloaddition elimination reaction; Thiocarbonyl compounds; Thiopyrans

Indexed keywords

1,3 OXATHIANE DERIVATIVE; ALKENE; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; POLYMERIZATION; SYNTHESIS;

EID: 0034650602     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02064-X     Document Type: Article

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31. 1,3-Oxathianes 1a,b were easily prepared from 3-mercapto-3-methyl-1-butanol and the corresponding aldehydes catalyzed by boron trifluoride etherate in high yields.
32. The stereochemistry was determined by NOE experiments between the methyl proton and the methine proton adjacent to the phenyl ring of the diastereomer cis-3ab (Table 1, entry 2) isolated by silica gel chromatography. The cis and trans stereochemistry of the other compounds was determined by comparison of the chemical shifts of the olefinic protons of 3,4-dihydro-2H-thiopyran 3.