title: The rearrangement route to 3-CH(2)X-2-azabicyclo[2.1.1]hexanes. Substituent control of neighboring group participation.
abstract: The stereocontrolled synthesis of a functionalized 3-hydroxymethyl-2-azabicyclo[2.1.1]hexane synthon for a variety of methano-bridged pyrrolidines has been effected. The key step in an electrophilic addition-rearrangement route uses a 3-nosyloxymethyl group in the 2-azabicyclo[2.2.0]hex-5-ene precursor in order to suppress unwanted competitive oxygen neighboring group participation. [reaction: see text]
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, PA 19122, USA. grantkrow@aol.com
authors.forename: Grant R
authors.initials: GR
authors.lastname: Krow
authors.forename: Jing
authors.initials: J
authors.lastname: Yuan
authors.forename: Guoliang
authors.initials: G
authors.lastname: Lin
authors.forename: Philip E
authors.initials: PE
authors.lastname: Sonnet