Exploiting the regioselectivity of pyroglutamate alkylations for the synthesis of 6-azabicyclo[3.2.1]octanes and 4-azabicyclo[3.3.0]octanes

K.G.R. Masschelein, C.V. Stevens, N. Dieltiens, D.D. Claeys
Tetrahedron
63 (22), 4712–4724
2007
A1

Abstract 

Depending on the N-protecting group of pyroglutamates, the reactivity can be directed to the formation of 6-azabicyclo[3.2.1]octanes or 4-azabicyclo[3.3.0]octanes, which are conformationally restricted glutamate analogues.