Carbonyl allylations by 3-halopropenes or 2-propenyl mesylate with tin(IV) chloride and tetrabutylammonium iodide

Tetrahedron Letters

Volumn 44, Issue 14, 2003, Pages 2845-2847

  Masuyama, Yoshiro ^a   Suga, Takanori ^a   Watabe, Akiko ^a   Kurusu, Yasuhiko ^a  

^a SOPHIA UNIVERSITY   (Japan)

Author keywords

Allylations; Allylic tins; Homoallylic alcohols; Nucleophilic additions; Tin(IV) chloride

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; MESYLIC ACID DERIVATIVE; PROPYLENE; TETRABUTYLAMMONIUM; TIN CHLORIDE;

ALLYLATION; ARTICLE; COLUMN CHROMATOGRAPHY; PURIFICATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037474602     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00469-6     Document Type: Article

References (28)

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23. For in situ preparation of allylic tins in nonpolar solvents except for the reaction of allylic compounds such as allylic halides, alcohols or esters with tin(II) halides, see: (a) Ref. 2a; (b) Masuyama, Y.; Saeki, K.; Horiguchi, S.; Kurusu, Y. Synlett 2001, 1802.
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26. 2. See: Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577.
27. 4-TBAI because of the failure of preparing 2-butenyl mesylate from 2-buten-1-ol and methanesulfonyl chloride under various conditions.
28. 13C NMR spectra with those of an authentic sample prepared from tetrabutylammonium iodide and iodine, similarly to Ref. 9.