title: Effective 1,5-, 1,6- and 1,7-remote stereocontrol in reactions of alkoxy- and hydroxy-substituted allylstannanes with aldehydes.
abstract: Alk-2-enylstannanes with 4-, 5- and 6-alkoxy- or -hydroxy-substituents are transmetallated stereoselectively with tin(iv) halides to generate allyltin trihalides which react with aldehydes to give (Z)-alk-3-enols with useful levels of 1,5-, 1,6- and 1,7-stereocontrol. Alk-2-enylstannanes with a stereogenic centre bearing a hydroxy or alkoxy group at the 4-, 5- or 6-position, react with overall (Z)-1,5-, 1,6- and 1,7-syn-stereoselectivity with respect to the hydroxy and alkoxy substituents. The analogous reactions of alkoxy- and -hydroxyalk-2-enylstannanes with a methyl bearing stereogenic centre at the 4- or 5-position react with overall (Z)-1,5- and 1,6-anti-stereoselectivity with respect to the hydroxy and methyl substituents.
authors.affiliation: School of Chemistry, University of Manchester, Manchester, UK.
authors.forename: John S
authors.initials: JS
authors.lastname: Carey
authors.forename: Somhairle
authors.initials: S
authors.lastname: MacCormick
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Stanway
authors.forename: Aphiwat
authors.initials: A
authors.lastname: Teerawutgulrag
authors.forename: Eric J
authors.initials: EJ
authors.lastname: Thomas