Robinson, Richard I. and Stephens, John C. and Worden, Steve M. and Blake, Alexander J. and Wilson, Claire and Woodward, Simon (2004) Sulfonic Acid Libraries Attained Through Opening of 2-Sulfobenzoic Acid Anhydride. European Journal of Organic Chemistry, 2004 (22). pp. 4596-4605. ISSN 1434-193X

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Abstract

2-Sulfobenzoic acid anhydride opens cleanly with N-Boc-protected α-amino alcohols to afford zwitterionic esters 1,2-C6H4(SO3−)(CO2CH2CHR1NH3+) (R1 = H, alkyl), the species R1 = iPr is crystallographically characterised. Dehydration of these species affords zwitterionic oxazoline sulfonic acid derivatives 1,2-C6H4(SO3−)(CA=NH+CHR1CH2OA) (CA and OA are bonded C−O) for R1 = iPr (X-ray), iBu, tBu, CH2Ph. Reaction with water regenerates the zwitterionic esters while exposure to M(OAc)2 (M = Cu, Pd) leads to the formation of the crystallographically characterised complexes MIIL2 (L = anion of the iPr-oxazolinesulfonic acid). Heating either the zwitterionic esters or oxazolines with R2NH2 [R2 = CH2Ph, CH2(1-C10H7), R-CH(Me)Ph] leads to SN2 attack at the oxazoline methylene group leading to the amido sulfonic acids 1,2-C6H4(CONHCHRCH2NHR2)(SO3H) based on crystallographic studies on R1 = iPr, R2 = CH2(1-C10H7).

Item Type:	Article
Keywords:	Molecular diversity; Amino alcohols; Sulfonic acids; S ligands; N,O ligands; Hydrogen bonding;
Academic Unit:	Faculty of Science and Engineering > Chemistry
Item ID:	7821
Identification Number:	https://doi.org/10.1002/ejoc.200400562
Depositing User:	Dr John Stephens
Date Deposited:	27 Jan 2017 15:28
Journal or Publication Title:	European Journal of Organic Chemistry
Publisher:	Wiley
Refereed:	Yes
Funders:	European Commission
URI:	http://onlinelibrary.wiley.com
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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