Chemical and Mechanistic Studies of Alpha' Lithio Amides

The lithiation and electrophilic substitution of the allyl amides, N-allyl-N-methyl-2-ethyl-methylbutanamide (76), 1,2,5,6-tetrahydropyridinyl-2-ethyl-2-methylbutanamide (77), 3-methylene-2-ethyl-2-methylbutanamide (78) and 5-tert-butyl-1,2,5,6-tetrahydropyridinyl-2-ethyl-2-methylbutanamide (79) is reported. The α\sp\prime lithio amides from 76, 77, and 79 are found to react with a variety of electrophiles in moderate yields to give both α and γ substituted products, and the α\sp\prime lithio amide 78 which has the geometry of the anion in E configuration, gives only poor yields. High diastereoselectivity in the reaction products from the α\sp\prime lithio amide from 79 is found.

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

2014

Author dc:creator

• Lee, Burnell

Contributors dc:contributor

• Beak, Peter

• Chemistry, Organic

Identifier

(UMI)AAI8803107

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70389