A Bicyclic L-Proline Derived Chiral Auxiliary for Asymmetric Synthesis

This thesis describes the use of an L−proline-derived chiral auxiliary for diastereoselective lithiation and ligand synthesis. Such compounds have been utilized in the Metallinos research group previously for the synthesis of N−substituted planar chiral ferrocenes. The first project describes the use of this chiral auxiliary as a directing group for N−benzyl substitution, providing products in up to 10:1 diastereomeric ratio (dr). These derivatives may serve as chiral ylidene precursors to serve as ligands in transition metal catalysis. In addition, an N−substituted planar chiral ferrocene ylidene ligand derived from the same chiral auxiliary was used to prepare rhodium complexes that were explored as potential catalysts for asymmetric hydroformylation.

Pay roll voucher #13 from the Engineer Department of Port Dalhousie and Thorold Railway Extension for the Northern Division for the month of April, 1857 approved by F. Shanly, chief engineer and W.G. Thompson, assistant engineer, April 27, 1857

Pay roll voucher #13 from the Engineer Department of Port Dalhousie and Thorold Railway Extension for the Northern Division for the month of April, 1857 approved by F. Shanly, chief engineer and W.G. Thompson, assistant engineer, April 27, 1857.

Pay roll voucher #14 from the Engineer Department of Port Dalhousie and Thorold Railway Extension for the Southern Division for the month of April, 1857 approved by F. Shanly, chief engineer and Francis A. Doyle, assistant engineer, April 28, 1857

Pay roll voucher #14 from the Engineer Department of Port Dalhousie and Thorold Railway Extension for the Southern Division for the month of April, 1857 approved by F. Shanly, chief engineer and Francis A. Doyle, assistant engineer, April 28, 1857.

Pay roll voucher # 17 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Northern Division for the month of May, 1857, approved by F. Shanly, chief engineer and W.G. Thompson, assistant engineer, May 27, 1857

Pay roll voucher # 17 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Northern Division for the month of May, 1857, approved by F. Shanly, chief engineer and W.G. Thompson, assistant engineer, May 27, 1857.

Pay roll voucher #18 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Southern Division approved by F. Shanly, chief engineer and F.A. Doyle assistant engineer, May 31, 1857

Pay roll voucher #18 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Southern Division approved by F. Shanly, chief engineer and F.A. Doyle assistant engineer, May 31, 1857.

Voucher from the Engineer Department of Port Dalhousie and Thorold Railway Extension for W.G. Thompson for the Northern Division. There are attached notes from the Welland Railway Company to John Mitchell for putting up shelves; to William Waud, staff; and to William Martin to repair the office (copy), June 10, 1857

Voucher from the Engineer Department of Port Dalhousie and Thorold Railway Extension for W.G. Thompson for the Northern Division. There are attached notes from the Welland Railway Company to John Mitchell for putting up shelves; to William Waud, staff; and to William Martin to repair the office (copy), June 10, 1857.

Pay roll voucher #20 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Northern Division approved by F. Shanly, chief engineer and W.G. Thompson, assistant engineer (copy) June 1857

Pay roll voucher #20 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Northern Division approved by F. Shanly, chief engineer and W.G. Thompson, assistant engineer (copy) June 1857.

Pay roll voucher #21 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Southern Division approved by F. Shanly, chief engineer and Francis A. Doyle, assistant engineer (copy) June 29, 1857

Pay roll voucher #21 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Southern Division approved by F. Shanly, chief engineer and Francis A. Doyle, assistant engineer (copy) June 29, 1857.

Pay roll voucher #26 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Southern Division, for the month of July, 1857 approved by F. Shanly, chief engineer and Francis A. Doyle (copy), July 28, 1857

Pay roll voucher #26 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Southern Division, for the month of July, 1857 approved by F. Shanly, chief engineer and Francis A. Doyle (copy), July 28, 1857.

Pay roll voucher #25 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Northern Division, for the month of July, 1857 approved by F. Shanly, chief engineer and W. G. Thompson (copy), July 30, 1857

Pay roll voucher #25 from the Engineer Department of Port Dalhousie and Thorold Railway Extension, for the Northern Division, for the month of July, 1857 approved by F. Shanly, chief engineer and W. G. Thompson (copy), July 30, 1857.

Pay roll voucher #30 from the Engineer Department of the Welland Railway for the Southern Division for the month of August, Aug. 31, 1857

Pay roll voucher #30 from the Engineer Department of the Welland Railway for the Southern Division for the month of August, Aug. 31, 1857.

Pay roll voucher #33 from the Engineer Department of the Welland Railway for the Southern Division

Pay roll voucher #33 from the Engineer Department of the Welland Railway for the Southern Division for the month of September. (2 copies) [one is signed on the 30th and one on the 31st], Sept. 31, 1857.

Pay roll voucher #32 from the Engineer Department of the Welland Railway for the Northern Division for the month of September

Pay roll voucher #32 from the Engineer Department of the Welland Railway for the Northern Division for the month of September, Oct. 2, 1857.

Pay roll voucher #36 from the Engineer Department of the Welland Railway for the Northern Division for the month of October

Pay roll voucher #36 from the Engineer Department of the Welland Railway for the Northern Division for the month of October, Nov. 3, 1857.

Pay roll voucher #37 from the Engineer Department of the Welland Railway for the Southern Division for the month of October

Pay roll voucher #37 from the Engineer Department of the Welland Railway for the Southern Division for the month of October, Nov. 6, 1857.