Novel syntheses by directed lithiations of N-Boc benzylamines and cyclopropylamines
Park, Yong Sun
This item is only available for download by members of the University of Illinois community. Students, faculty, and staff at the U of I may log in with your NetID and password to view the item. If you are trying to access an Illinois-restricted dissertation or thesis, you can request a copy through your library's Inter-Library Loan office or purchase a copy directly from ProQuest.
Permalink
https://hdl.handle.net/2142/19974
Description
Title
Novel syntheses by directed lithiations of N-Boc benzylamines and cyclopropylamines
Author(s)
Park, Yong Sun
Issue Date
1996
Doctoral Committee Chair(s)
Beak, Peter
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
The lithiation-substitution of N-Boc benzylamines and cyclopropylamines have been investigated to explore the synthetic potential of these substrates. We have achieved the syntheses of highly enantioenriched benzylic $\alpha$-substituted N-Boc secondary amines using RLi/(-)-sparteine. Extension of this chemistry to asymmetric syntheses of both enantiomers of primary $\alpha$-substituted benzylamines and $\alpha,\alpha$-disubstituted benzylamines has been achieved successfully. Also, the N-Boc group was used as an activating and directing group for the $\alpha$ and $\beta$ lithiation-substitution of cyclopropanes. Extension of this chemistry to syntheses of highly functionalized cyclopentane by (3 + 2) cycloaddition and asymmetric synthesis of N-Boc azabicyclic (3.10) hexane was investigated.
Use this login method if you
don't
have an
@illinois.edu
email address.
(Oops, I do have one)
IDEALS migrated to a new platform on June 23, 2022. If you created
your account prior to this date, you will have to reset your password
using the forgot-password link below.
