title: Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes.
abstract: The scope of the copper-catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete γ-E-selectivity and preferential 1,3-syn stereoselectivity. The reaction of γ-silicon-substituted allylic phosphates affords enantioenriched α-stereogenic allylsilanes.
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810 (Japan), ;http://wwwchem.sci.hokudai.ac.jp/∼orgmet/index.php.
authors.forename: Yuto
authors.initials: Y
authors.lastname: Yasuda
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810 (Japan), ;http://wwwchem.sci.hokudai.ac.jp/∼orgmet/index.php.
authors.forename: Kazunori
authors.initials: K
authors.lastname: Nagao
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810 (Japan), ;http://wwwchem.sci.hokudai.ac.jp/∼orgmet/index.php.
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Shido
authors.affiliation: Faculty of Science, Ibaraki University, Mito 310-8512 (Japan).
authors.forename: Seiji
authors.initials: S
authors.lastname: Mori
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810 (Japan), ;http://wwwchem.sci.hokudai.ac.jp/∼orgmet/index.php. ohmiya@sci.hokudai.ac.jp.
authors.forename: Hirohisa
authors.initials: H
authors.lastname: Ohmiya
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810 (Japan), ;http://wwwchem.sci.hokudai.ac.jp/∼orgmet/index.php. sawamura@sci.hokudai.ac.jp.
authors.forename: Masaya
authors.initials: M
authors.lastname: Sawamura
keywords: allylic substitution; copper catalysis; coupling; secondary alkylborane; stereoselectivity