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Synthesis 2018; 50(24): 4777-4795
DOI: 10.1055/s-0037-1610311
DOI: 10.1055/s-0037-1610311
short review
Macrocyclic Hosts in Asymmetric Phase-Transfer Catalyzed Reactions
The University of Salerno is gratefully acknowledged for funding (FARB).Further Information
Publication History
Received: 27 August 2018
Accepted after revision: 28 September 2018
Publication Date:
22 October 2018 (online)
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
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For selected examples:
For selected examples:
For selected examples of highly enantioselective alkylation with alkyl halides see:
For examples of highly enantioselective Michael addition with vinyl acceptors, see:
For more enantioselective additions of N-(diphenylmethylene)glycine esters to acrylonitrile under PTC conditions, see:
For selected examples, see:
For selected examples see:
For improved procedures using tetramethylammonium fluoride as a source of fluoride ion, see:
For selected examples, see:
For reviews, see:
For reviews, see: