Stereoselective synthesis of 5-substituted pyrrolo[1,2-c]imidazol-3-ones. Access to aldosterone synthase inhibitors and chiral precatalysts

Compounds containing the pyrrolidine moiety are key substructures of compounds with biological activity and organocatalysts. In particular, annulated chiral pyrrolidines with alpha stereogenic centers have aldostereone synthase inhibition activity. In addition, 5-substituted pyrroloimidazol(in)ium salts precursors to N-heterocyclic carbene (NHC) precatalysts are rare due to a lack of convenient synthetic routes to access them. In this thesis is described a rapid synthesis of NHC precursors and a possible route to 5-substituted pyrroloimidazole biologically active compounds. The method involves the preparation of chiral saturated and achiral unsaturated pyrrolo[I,2- c]imidazol-3-ones from N-Cbz-protected t-Butyl proline carboxamide. The resulting starting materials may be used to prepare the target chiral annulated imidazol(in)ium products by a two-step sequence involving first stereoselective lithiation-substitution, followed by POCh induced salt formation.

Second Welland Canal - Book 1, Survey Map 10 - St. Catharines

Survey map of the Second Welland Canal created by the Welland Canal Company along the western edge of the Town of St. Catharines. Although not labelled, the Second Welland Canal can be seen running through the map along with its tow path, which is located on the southwestern edge of the waterway. The surveyors' measurements and notes can be seen in red and black ink and pencil. Local area landmarks are identified and include streets and roads (ex. Ontario Street and Road to Hamilton), Artesian Mineral Well, Dr. Mack's Artesian Well, Stephenson House Mineral Well and Gas Works, New Brewery, Old Brewery, Welland House Mineral Well, L. Shickluna's Shipyard, Vinegar Manufactory, Merritt's Covered Race, Mitchels Wharf, Sail Loft, an office, a tavern, two barns, a boathouse, a structure belonging to T. Nihan (or P. Nihen), and some store houses. Properties and property owners of note are: Concession 6 Lot 20, William H. Merritt, E. S. Adams, William Chace, Jacob Hainer, J. Taylor, and J. P. Merritt.

Second Welland Canal - Book 3, Survey Map 1 - Canal to Chippewa Creek with Port Robinson

Survey map of the Second Welland Canal created by the Welland Canal Company showing Port Robinson and the canal to Chippewa Creek. The surveyors' measurements and notes can be seen in red and black ink and pencil. Local area landmarks are also identified and include streets and roads (ex. Front Street, Bridge Street, and Cross Street), the Welland railroad, Dry Dock leased to D. McFarland and Abbey, G. Jordan Tavern, D. McFarland and Co. Burnt Saw Mill, I. Pew Shop, Old Locks, New Lock, Canal to Chippewa Creek, Chippewa Creek, covered drain from dry dock, a barn and several bridges. Properties and property owners of note are: Lots 202, Broken Front lots 202 and 203, D. McFarland, and G. Jordan.