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Title:Lewis Base Catalysis: I. Catalytic Enantioselective Aldol Additions of Methyl Trichlorosilyl Ketene Acetal to Ketones. II. Catalytic Enantioselective Alpha-Additions of Isocyanides to Aldehydes
Author(s):Fan, Yu
Doctoral Committee Chair(s):Denmark, Scott E.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract: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.
Issue Date:2004
Type:Text
Language:English
Description:440 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2004.
URI:http://hdl.handle.net/2142/84134
Other Identifier(s):(MiAaPQ)AAI3130914
Date Available in IDEALS:2015-09-25
Date Deposited:2004


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