The rearrangement route to 3-CH(2)X-2-azabicyclo[2.1.1]hexanes. Substituent control of neighboring group participation.
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]
Krow
Grant R
GR
Department of Chemistry, Temple University, Philadelphia, PA 19122, USA. grantkrow@aol.com
Yuan
Jing
J
Lin
Guoliang
G
Sonnet
Philip E
PE