title: An intramolecular [2 + 2] photocycloaddition approach to conformationally restricted bis-pyrrolidines.
abstract: With N-Boc-protected 4-(allylaminomethyl)-2(5H)furanones as starting materials, a photochemical approach is presented to give 3,9-diazatricyclo[5.3.0.0(1,5)]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 C2 symmetry. When the furanones had a phenyl group at the 3-position (X(3)), alternative photochemical pathways were observed.
authors.affiliation: Lehrstuhl für Organische Chemie I, Technische Universität München , Lichtenbergstrasse 4, 85747 Garching, Germany.
authors.forename: Diego A
authors.initials: DA
authors.lastname: Fort
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Woltering
authors.forename: André M
authors.initials: AM
authors.lastname: Alker
authors.forename: Thorsten
authors.initials: T
authors.lastname: Bach
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry*; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D010777:Photochemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011083:Polycyclic Compounds; D011759:Pyrrolidines; D015107:4-Butyrolactone