The rearrangement route to 3-carboxy- and 3-hydroxymethyl-2-azabicyclo[2.1.1]hexanes: 3,5-methanoprolines.
Improved stereocontrolled syntheses of 5-anti-hydroxy-3-exo-methoxycarbonyl-2-azabicyclo[2.1.1]hexanes have been effected from pyridine. The key step in the electrophilic addition-rearrangement of 2-azabicyclo[2.2.0]hex-5-ene precursors incorporates either a 3-endo-phenyl group, as an acid precursor, or a 3-endo-phenyldimethylsilylmethyl group, as a potential hydroxymethyl and acid precursor.
Krow
Grant R
GR
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. grantkrow@aol.com
Lin
Guoliang
G
Yu
Fang
F