Regioselective Michael-induced cyclisation of γ- and δ-hydroxy vinyl sulfides and vinyl dithiocarbamates

Tetrahedron Letters

Volumn 46, Issue 25, 2005, Pages 4349-4352

  Aucagne, V ^a   Lorin, C ^b   Tatibouet A ^a   Rollin, P ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b UNIVERSITY OF APPLIED SCIENCES AND ARTS NORTHWESTERN SWITZERLAND   (Switzerland)

Author keywords

C glycosides; Hetero Michael additions; Vinyl dithiocarbamates; Vinyl sulfides

Indexed keywords

ANION; CHELATING AGENT; GLYCOSIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFIDE; VINYL DERIVATIVE;

ARTICLE; BIODIVERSITY; CHELATION; CYCLIZATION; ELECTRON; MICHAEL ADDITION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 19444378503     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.112     Document Type: Article

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15. Interestingly, during our attempts to optimise the conditions for the cyclisation of 1a, it was found that addition of a stoichiometric amount of various electrophiles could be beneficial to the reaction in terms of the yield. The best results were obtained with tosyl chloride, which dramatically raised the yield up to 88%. This 'electrophilic assistance' seemed to be limited to the benzothiazolyl moiety and could not be extended to the other heteroaryl derivatives: γ,δ-epoxy derivatives were the major products obtained in the tosyl chloride-activated reaction of 1b-e in phase transfer conditions
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19. 2: calcd. 405.1644; found 405.1631