Macrocyclic Hosts in Asymmetric Phase-Transfer Catalyzed Reactions

Rosaria Schettini; Marina Sicignano; Francesco De Riccardis; Irene Izzo; Giorgio Della Sala

doi:10.1055/s-0037-1610311

Synthesis, Table of Contents

Synthesis 2018; 50(24): 4777-4795
DOI: 10.1055/s-0037-1610311

short review

Macrocyclic Hosts in Asymmetric Phase-Transfer Catalyzed Reactions

Rosaria Schettini

,

Marina Sicignano

,

Francesco De Riccardis

,

Irene Izzo

,

Giorgio Della Sala *

Dipartimento di Chimica e Biologia ‘A. Zambelli’, Università degli Studi di Salerno, Via Giovanni Paolo II 132, 84084 Fisciano (SA), Italy Email: gdsala@unisa.it

› Author Affiliations

Abstract

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Abstract

The introduction and development of neutral macrocyclic hosts capable of complexing ions within their pre-organized cavity, has been of utmost importance in supramolecular chemistry. Their ability to form stable organic-soluble metal–macrocycle complexes opened up the way to their application in phase-transfer catalysis (PTC) as a viable alternative to quaternary onium salts. In particular, their conformationally rigid preorganized backbone, accommodating organic substrates in defined orientations, promotes highly efficient stereoselective reactions. This short review summarizes the applications of neutral macrocyclic hosts in stereoselective PTC, highlighting the difference and possible complementarity with quaternary ammonium salts.

1 Introduction

2 Crown Ethers and Related Coronands

2.1 Enantioselective PTC with Chiral Macrocyclic Coronands

2.2 Enantioselective PTC Reactions Catalyzed by Chiral Quaternary Ammonium Salts with Achiral Crown Ether Co-catalysts

3 Cyclic Peptoids

4 Miscellaneous Chiral Macrocyclic Hosts

5 Summary and Outlook

Key words

asymmetric catalysis - crown compounds - host-guest systems - macrocycles - phase-transfer catalysis - calixarenes - cyclic peptoids

Full Text

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