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University of Illinois at Urbana-Champaign
Lewis Base Catalysis: I. Catalytic Enantioselective Aldol Additions of Methyl Trichlorosilyl Ketene Acetal to Ketones. II. Catalytic Enantioselective Alpha-Additions of Isocyanides to Aldehydes
Abstract
dc:descriptionThe 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.
Degree
thesis:*- Name thesis:degree_name
- Ph.D.
- Level thesis:degree_level
- Dissertation
- Discipline thesis:degree_discipline
- Chemistry
- Grantor
- University of Illinois at Urbana-Champaign
- Year dc:date
- 2015
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Fan, Yu
- Contributors dc:contributor
-
- Denmark, Scott E.
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI3130914
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84134