19781-54-5Relevant articles and documents
Faulkner,D.J.,Petersen,M.R.
, p. 3243 - 3246 (1969)
Stereoselective synthesis of trisubstituted olefins by a directed allylic substitution strategy
Schmidt, Yvonne,Breit, Bernhard
supporting information; experimental part, p. 11780 - 11788 (2011/11/06)
New methodology for the stereoselective synthesis of trisubstituted olefins is presented. The use of ortho-diphenylphosphanyl benzoate (o-DPPB) as a directing leaving group for copper-mediated allylic substitution with Grignard reagents allowed for the stereoselective construction of a wide range of E olefins, without the need for an adjacent electron-withdrawing group. Our modular three-step approach toward trisubstituted alkenes commenced with geminal α-methylene aldehydes. Addition of an organometallic reagent and introduction of the o-DPPB group by esterification was followed by the o-DPPB-directed copper-mediated allylic substitution with a Grignard reagent to furnish stereodefined trisubstituted olefins. Additionally, incorporation of a stereocenter from the chiral pool allowed the preparation of an enantiomerically pure olefin that bore three alkyl substituents in high E/Z selectivity.
Stereoselective synthesis of cis-β-methyl- and phenyl-substituted alkenylboronates by platinum-catalyzed dehydrogenative borylation
Ohmura, Toshimichi,Takasaki, Yuta,Furukawa, Hideki,Suginome, Michinori
supporting information; body text, p. 2372 - 2375 (2009/08/19)
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