title: Novel functionalized titanium(IV) benzylidenes for the traceless solid-phase synthesis of indoles.
abstract: [reaction: see text] Titanium(IV) benzylidenes bearing a masked nitrogen nucleophile in the ortho position converted Merrifield resin-bound esters into enol ethers. An unusual nitrogen protecting group, N-silylated tert-butyl carbamate, was employed. One percent TFA released N-Boc indoles in high yield and purity. N-Methyl indoles were also prepared. Cyclative termination was not required to release the chameleon catch. The first example of a carbonyl group within a titanium alkylidene reagent is reported.
authors.affiliation: Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.
authors.forename: Calum
authors.initials: C
authors.lastname: Macleod
authors.forename: Richard C
authors.initials: RC
authors.lastname: Hartley
authors.forename: Dieter W
authors.initials: DW
authors.lastname: Hamprecht