Facile double nucleophilic addition of thiols and tetraallyltin to latent 2-alkynals using in situ hydrolysis of the imino functionality promoted by tin(IV) chloride pentahydrate

Synlett

Volumn , Issue 10, 2003, Pages 1469-1473

  Shimizu, Makoto ^a   Nishi, Takafumi ^a   Yamamoto, Akihiro ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

Alkynes; Conjugate addition; Imino compound; Lewis acid; Vinyl sulfide

Indexed keywords

ALKANE DERIVATIVE; LEWIS ACID; THIOL DERIVATIVE; TIN; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DIASTEREOISOMER; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0043198256     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40857     Document Type: Article

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24. 4) and concentrated in vacuo to give a crude oil. Purification on silica gel TLC (n-hexane:EtOAc = 4:1 as an eluent) gave (Z)-1-benzylthio-1-phenylhexa-1,5-dien-3-ol (47.6 mg, 84%) as a colorless oil.
25. 4 was used as a Lewis acid, only 1,4-addition of thiol was observed.
26. The olefin geometry was determined using the NOESY experiment.