Authors

Paul W. Erhardt

Abstract

This invention relates to the use of a family of chiral α-substituted benzylamine reagents during chemical synthesis. Specifically, the reagents can be used in an auxiliary manner to deliver either a substituted or unsubstituted nitrogen atom while simultaneously bestowing an asymmetric bias toward the formation and separation of the diastereomeric intermediates that result from reaction of the reagents with racemic substrates also having one or more asymmetric atoms. The chiral auxiliary portion of the reagents can then be readily removed at some later and convenient stage of the overall synthetic scheme. The initial nitrogen-delivery reaction, asymmetric separation procedures, and removal of the chiral auxiliary can all be conducted under routine experimental conditions, including the final debenzylation, such that the overall method is adaptable to large-scale chemistry. Since the reagents are particularly useful whenever a nitrogen-containing system has alpha- , beta- or gamma-asymmetry, the latter being a common structural motif within many pharmaceutical agents, the methods are of primary utility for the laboratory preparation and large-scale manufacture of enantimerically pure drug molecules.

Document Type

Patent

Primary Class

564/303

Secondary Class

564/302

Application Number

09/059990

Filing Date

April 1998

Patent Number

US5977409

Assignee(s)

The University of Toledo

Publication Date

11-2-1999

Patent Country

US

Language

en_US

Institution

The University of Toledo

Repository

University of Toledo Libraries

Digital Publisher

Digital Initiatives

Rights

These materials are free of copyright restrictions and are in the public domain within the United States only. The USPTO reserves the right to assert copyright protection internationally.

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Rights Statement

No Copyright - United States. URI: http://rightsstatements.org/vocab/NoC-US/1.0/
The organization that has made the Item available believes that the Item is in the Public Domain under the laws of the United States, but a determination was not made as to its copyright status under the copyright laws of other countries. The Item may not be in the Public Domain under the laws of other countries. Please refer to the organization that has made the Item available for more information.