On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

Steven D. Bull; Stephen G. Davies; A. Christopher Garner; Alastair L. Parkes; Paul M. Roberts; Thomas G. R. Sellers; Andrew D. Smith; Juan A. Tamayo; James E. Thomson; Richard J. Vickers

doi:10.1039/B701628J

skip RSC | ChemSpider | Feedback

Home > Journals > New Journal of Chemistry > On the origins of diast...

Authors & Referees | Librarians

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

New Journal of Chemistry

Issue 4, 2007

In partnership with Centre National de la Recherche Scientifique
More about this Journal
Editorial Board
Submit an Article

Follow Journal |

Journal Home | RSC Journals

Paper

Previous Article | Next Article

On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

Steven D. Bull , Stephen G. Davies , A. Christopher Garner , Alastair L. Parkes , Paul M. Roberts , Thomas G. R. Sellers , Andrew D. Smith , Juan A. Tamayo , James E. Thomson and Richard J. Vickers

New J. Chem., 2007, 31, 486-495

DOI: 10.1039/B701628J
Received 02 Feb 2007, Accepted 01 Mar 2007
First published on the web 09 Mar 2007

Please wait while Download options loads

Request Permissions

Abstract
Cited by
Related Content

High levels of diastereoselectivity are observed for benzylation of the lithium enolates of (S)-N,N′-bis-para-methoxybenzyl-3-iso-propyl-piperazine-2,5-dione, (S)-N(1)-para-methoxybenzyl-N(4)-methyl-3-iso-propyl-piperazine-2,5-dione and (S)-N(1)-methyl-N(4)-para-methoxybenzyl-3-iso-propyl-piperazine-2,5-dione. These data suggest that the high diastereofacial selectivity observed for alkylation of these diketopiperazine templates is mainly a consequence of the relay of stereochemical information from C(3) to C(6) via the influence of 1,2-torsional strain introduced by the N-alkyl substituents, rather than through minimisation of steric interactions alone.

Terms & Conditions|Privacy |Accessibility|ACAP Enabled

New Journal of Chemistry

On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

Log in (Free Access)

Log in (Subscriber Access)

Articles By