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Description
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 |
This item appears in the following Collection(s)
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Dissertations and Theses - Chemistry
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Graduate Dissertations and Theses at Illinois
Graduate Theses and Dissertations at Illinois