2026-09-21T18:25:42Z https://www.ideals.illinois.edu/oai-pmh

oai:www.ideals.illinois.edu:2142/84134 2023-07-11 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

2015-09-25T22:13:06Z 10000-01-01 2004 2004 Denmark, Scott E. Fan, Yu 2015-09-25T22:13:06Z The first catalytic, enantioselective alpha-addition reaction of isocyanides has been demonstrated with a SiCl4·bisbinaphthyldiamine phosphoramide catalyst. Good yields have been obtained with aromatic, heteroaromatic, conjugated non-aromatic and non-branched aliphatic aldehydes. Aromatic, aliphatic and functionalized isocyanides provided high yields of alpha-addition products. Enantiomeric ratios ranging from 92/2 to 99/1 have been achieved in the addition of tert-butyl isocyanide to aromatic aldehydes. The imidoyl chloride intermediates has been directly converted into chiral alpha-hydroxy amides and carboxylic esters without loss in enantiomeric purity. Made available in DSpace on 2015-09-25T22:13:06Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 3130914.pdf: 10372329 bytes, checksum: 91a9052e37f4f5eeb0e3e03528fb2a71 (MD5) Previous issue date: 2004 Embargo set by: Seth Robbins for item 85415 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 440 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2004. http://hdl.handle.net/2142/84134 (MiAaPQ)AAI3130914 eng Chemistry, Organic Lewis Base Catalysis: I. Catalytic Enantioselective Aldol Additions of Methyl Trichlorosilyl Ketene Acetal to Ketones. II. Catalytic Enantioselective Alpha-Additions of Isocyanides to Aldehydes text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.