Eric J. Enholm

One electron C-C bond forming reactions VIA allylstannanes: Scope and limitations

Abstract Free radical (or “one-electron”) methodology for carbon-carbon bond forming reactions using allylstannanes is described in detail. Such reactions have the advantages of tolerating quite complex functionality in the substrate and of being nearly stoichiometric in reagents, and not requiring extensive experimentation for application to new substrates.

Observations on the choice of Lewis acid and mode of addition for the Lewis acid mediated reaction of crotyltri-n-butylstannane with aldehydes: convenient and highly selective access to both erythro and threo products

Abstract For additions crotyltri- n -butylstannane to simple aldehydes mediated by BF3·Et2O, erythro selectivity may be increased considerably (25:1 vs. 9:1, for example) by simply using 2 eq. of stannane, TiCl4 mediated additions give high erythro or threo selectivity depending simply on the order in which reactants are mixed; and other Lewis acids are also evaluated in such reactions.

Two new methods for the synthesis of C-glycosides

Abstract Thiophenyl glycosides are converted to C-glycosides by reaction with allyl or methallyltri- n -butylstannane using both “one-electron” and “two-electron” procedures, which give different stereoselectivities in some cases.

Synthetic studies on pyrrolizidine alkaloids. II. Intramolecular additions of radicals and electrophiles to allylstannanes as methods for ring closure

Abstract The simple pyrrolizidine alkaloid (±)-isoretronecanol was efficiently constructed by a route involving the attachment of an allylstannane moiety to succinimide followed by appropriate reduction, activation, and cyclization by either “one-electron” or “two-electron” protocols.