TY - JOUR
T1 - Oxidative fragmentation of bicyclic hydroxy silanes and stannanes
T2 - a strategy for the stereoselective synthesis of kainoids
AU - Clayden, Jonathan
AU - Hebditch, Katherine R.
AU - Read, Benjamin
AU - Helliwell, Madeleine
PY - 2007/11/26
Y1 - 2007/11/26
N2 - The addition of tin or silicon nucleophiles to bicyclic enones generated by dearomatising cyclisation gives stannanes and silanes stereoselectively. These compounds may be fragmented under oxidative conditions to generate substituted pyrrolidines bearing C2 and C3 substituents closely related to those found in the kainoid series of cyclic amino acids.
AB - The addition of tin or silicon nucleophiles to bicyclic enones generated by dearomatising cyclisation gives stannanes and silanes stereoselectively. These compounds may be fragmented under oxidative conditions to generate substituted pyrrolidines bearing C2 and C3 substituents closely related to those found in the kainoid series of cyclic amino acids.
UR - http://www.scopus.com/inward/record.url?scp=35548962680&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2007.09.150
DO - 10.1016/j.tetlet.2007.09.150
M3 - Article (Academic Journal)
AN - SCOPUS:35548962680
VL - 48
SP - 8550
EP - 8553
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 48
ER -