Enantioselective lateral lithiation-substitution of o-ethyl- and o-benzyl-N-pivaloylanilines: Studies of a pathway of stereoinformation transfer

The secondary amides o-ethyl-N-pivaloylaniline and o-benzyl-N-pivaloylaniline are laterally lithiated by sec-butyllithium to generate a dilithio intermediate. Electrophilic substitution of the organolithium in the presence of ($-$)-sparteine provides the products with enantiomeric excesses close to 80% for reactions with most electrophiles. The absolute configuration at the benzylic carbon is the same regardless of whether stannyl or stannyl chlorides, alkyl halides, or aldehydes and ketones are used as the electrophile.

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

2011

Author dc:creator

• Basu, Amit

Contributors dc:contributor

• Beak, Peter

• Chemistry, Organic

Statement dc:rights

• Copyright 1996 Basu, Amit

Language dc:language

eng

Identifier

9780591197402
AAI9712199
(UMI)AAI9712199

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/21964