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Application of divergent multi-component reactions in the synthesis of a library of peptidomimetics based on γ-amino-α,β-cyclopropyl acids

Wipf, P and Werner, S and Woo, GHC and Stephenson, CRJ and Walczak, MAA and Coleman, CM and Twining, LA (2005) Application of divergent multi-component reactions in the synthesis of a library of peptidomimetics based on γ-amino-α,β-cyclopropyl acids. Tetrahedron, 61 (48). 11488 - 11500. ISSN 0040-4020

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Abstract

The multi-component condensation of organozirconocene, aldimine and zinc carbenoid was applied to the stereoselective synthesis of cyclopropane amino acid derivatives. These compounds served as scaffolds for the preparation of a 46-member library. The C- and N-termini of the cyclopropane amino acid derivatives were diversified by condensations with ten amines and ten acylating agents, respectively. To improve yields and accelerate library synthesis, most products were prepared under microwave irradiation and purified by polymer-bound scavengers and SPE methodology. All compounds were analyzed by LC-MS and a representative selection was fully characterized. © 2005 Elsevier Ltd. All rights reserved.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Werner, S
Woo, GHC
Stephenson, CRJ
Walczak, MAA
Coleman, CM
Twining, LA
Date: 28 November 2005
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 61
Number: 48
Page Range: 11488 - 11500
DOI or Unique Handle: 10.1016/j.tet.2005.09.016
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 18 Jul 2014 21:02
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/22242

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