Studies of alpha-lithioamine synthetic equivalents: I. Elaboration of primary amines. II. Detection of an intermediate in the lithiation of a benzylic urea

Reagents for the α-substitution of N-Boc-benzylamine and N-Boc-allylamine have been developed via dilithiation and electrophilic substitution. Discussion of the specific conditions employed to accomplish these transformations is presented, as well as mechanistic speculation. Dilithiation and substitution of O-benzyl-N-methyl carbamate has been achieved, and use of sec-BuLi/(-)sparteine as the base provided the corresponding products with up to 57% enantiomeric excess. Lithiation of N-tert-butyl-N-benzyl carbamates resulted in rearrangement to phenylglycine derivatives. These related investigations are also discussed.

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

• Resek, James Edward

Contributors dc:contributor

• Beak, Peter

• Chemistry, Organic

Statement dc:rights

• Copyright 1994 Resek, James Edward

Language dc:language

eng

Identifier

AAI9416430
(UMI)AAI9416430

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/21980