title: Stereoretentive Addition of N-tert-Butylsulfonyl-α-Amido Silanes to Aldehydes, Ketones, α,β-Unsaturated Esters, and Imines.
abstract: Enantioenriched N-tert-butylsulfonyl-α-amido silanes were successfully reacted with aldehydes, ketones, imines, and α,β-unsaturated esters in the presence of a sub-stoichiometric amount of CsF (0.5 equiv) in 1,2-dimethoxyethane (DME) at -20 °C to afford the corresponding coupling products with up to 89 % enantiospecificity in a retentive manner.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo, 060-0812, Japan. tmita@pharm.hokudai.ac.jp.
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Mita
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo, 060-0812, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Saito
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo, 060-0812, Japan.
authors.forename: Masumi
authors.initials: M
authors.lastname: Sugawara
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo, 060-0812, Japan. biyo@pharm.hokudai.ac.jp.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sato
keywords: aldehydes; cesium fluoride; ketones; silanes; stereospecific reactions