TY - JOUR
T1 - An intramolecular [2 + 2] photocycloaddition approach to conformationally restricted bis-pyrrolidines
AU - Fort, Diego A.
AU - Woltering, Thomas J.
AU - Alker, André M.
AU - Bach, Thorsten
PY - 2014/8
Y1 - 2014/8
N2 - With N-Boc-protected 4-(allylaminomethyl)-2(5H)furanones as starting materials, a photochemical approach is presented to give 3,9-diazatricyclo[5.3. 0.01,5]decanes as conformationally restricted bis-pyrrolidines. The products are orthogonally protected at the two nitrogen atoms and exhibit, depending on the substitution pattern at positions C5, C6, and C7, latent C 2 symmetry. When the furanones had a phenyl group at the 3-position (X3), alternative photochemical pathways were observed.
AB - With N-Boc-protected 4-(allylaminomethyl)-2(5H)furanones as starting materials, a photochemical approach is presented to give 3,9-diazatricyclo[5.3. 0.01,5]decanes as conformationally restricted bis-pyrrolidines. The products are orthogonally protected at the two nitrogen atoms and exhibit, depending on the substitution pattern at positions C5, C6, and C7, latent C 2 symmetry. When the furanones had a phenyl group at the 3-position (X3), alternative photochemical pathways were observed.
UR - http://www.scopus.com/inward/record.url?scp=84905403814&partnerID=8YFLogxK
U2 - 10.1021/jo501302f
DO - 10.1021/jo501302f
M3 - Article
C2 - 24999855
AN - SCOPUS:84905403814
SN - 0022-3263
VL - 79
SP - 7152
EP - 7161
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 15
ER -