Title:
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Substrate Triggered Stereoselective Preparation of Highly Substituted Organic Carbonates
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Author:
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Laserna, Victor; Martin, Eddy; Escudero-Adán, Eduardo C.; Kleij, Arjan W.
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Abstract:
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Trisubstituted cyclic organic carbonates with multiple though well-defined stereochemical configurations are difficult to prepare. Here we present a conceptual design towards these CO2 based synthons using hydroxyl-substituted cyclic epoxide precursors and their catalytic conversion, to afford these challenging target compounds with fused ring sizes up to eight under excellent stereo-control. The observed stereochemistry of the organic carbonates combined with various control experiments revealed that these compounds are formed through a mechanistic manifold that involves a depolymerization reaction within an oligomeric carbonate induced by a pendent hydroxyl nucleophile. This manifold therefore provides an alternative approach towards CO2 valorization into functional, cyclic carbonate scaffolds of use in synthetic chemistry. |
Publication date:
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2017-07-07 |
Subject(s):
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54 |
Rights:
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L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/ |
Pages:
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5478 p. |
Document type:
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Article Article - Accepted version |
DOI:
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10.1021/acscatal.7b01748
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