Synthesis of tri-substituted vinyl boronates via ruthenium-catalyzed olefin cross-metathesis

Tetrahedron Letters

Volumn 45, Issue 41, 2004, Pages 7733-7736

  Morrill, Christie ^a   Funk, Timothy W ^a   Grubbs, Robert H ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Olefin cross metathesis; Ruthenium catalysis; Tri substituted alkenes; Vinyl boronates

Indexed keywords

ALKENE; BORONIC ACID DERIVATIVE; METHYL GROUP; RUTHENIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL PROCEDURES; CROSS METATHESIS; PINACOL REARRANGEMENT; SYNTHESIS;

EID: 4544235191     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.069     Document Type: Article

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30. Boronate 3 was synthesized according to the procedure given in Ref. 16
31. In the cross-metathesis reactions reported in both Tables 1 and 2, we sometimes observed the isomerization (ca. 5-20%) of the 1,1-disubstituted vinyl boronate starting material into its 1,2-isomer. In the case of boronate 3, we also sometimes observed the cross-metathesis of its 1,2-isomer with the other olefins in solution, which resulted in various 1,2-disubstituted vinyl boronate side products
32. Vinyl iodides were synthesized according to the procedure given in N. Kamiya, Y. Chikami, and Y. Ishii Synlett 11 1990 675 676 To obtain optimal results alcohols were protected as acetates during the reaction and subsequently deprotected. TBS protecting groups were not stable under these reaction conditions and thus had to be added after this reaction occurred
33. Vinyl iodides were converted to vinyl boronates according to the procedure given in J. Renaud, and S.G. Ouellet J. Am. Chem. Soc. 120 1998 7995 7996 Substrates containing free alcohols required 2.5 equiv. of n-butyllithium and pinacol borate reagent. In this procedure the pinacol borate was also added into the free alcohols but it was selectively removed by stirring the substrate in methanol (0.6 M) at room temperature for 4 h