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Issue 36, 2012
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Conformationally flexible chiral supramolecular catalysts for enantioselective Diels–Alder reactions with anomalous endo/exo selectivities

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Abstract

The potential of supramolecular catalysts to realize anomalous regio- and/or stereoselectivity in organic synthesis is highly attractive. To date, there have been a few examples of non-polymeric and non-covalent chiral supramolecular catalysts that induce practical enantioselectivity. In this regard, a metal–organic framework (MOF) may be one of the most important techniques for constructing conformationally rigid supramolecular catalysts. However, it is not easy to use the MOF technique to fine-tune a much more precise cage in catalysts for anomalous purposes. To establish high catalytic activity with anomalous regio- and/or stereoselectivity, in principle, an artificial cage should be conformationally flexible, like an active pocket in an enzyme with an induced-fit function. In this feature article, we focus on the anomalous endo/exo-selective Diels–Alder reaction, and overview the development of the successive catalysts including our recent highly active, conformationally flexible, and chiral supramolecular catalysts. The evolution from ‘ready-made’ single-molecule catalysts to ‘tailor-made’ supramolecular catalysts could offer not only high enantioselectivity but also high anomalous endo/exo-selectivities due to substrate-specific characteristics, as with enzymes.

Graphical abstract: Conformationally flexible chiral supramolecular catalysts for enantioselective Diels–Alder reactions with anomalous endo/exo selectivities

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Article information


Submitted
04 Jan 2012
Accepted
29 Feb 2012
First published
22 Mar 2012

Chem. Commun., 2012,48, 4273-4283
Article type
Feature Article

Conformationally flexible chiral supramolecular catalysts for enantioselective Diels–Alder reactions with anomalous endo/exo selectivities

M. Hatano and K. Ishihara, Chem. Commun., 2012, 48, 4273
DOI: 10.1039/C2CC00046F

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