2016
DOI: 10.3987/com-15-13394
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Inter- and Intramolecular Diels-Alder Reaction of Ethenetricarboxylate Derivatives

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Cited by 4 publications
(4 citation statements)
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“…They also reported that treatment of 22 with FeCl 3 underwent intramolecular reactions to give chlorinated γ-lactone with loss of stereochemistry on the side chain . The difference in stability can be explained, similar to the cyclization of other ethenetricarboxylate derivatives. , Triester 22 may be more stable in s- cis conformation of OC – O–CH 2 as shown in Scheme , probably because of the steric repulsion. In diester amide A (in Scheme ), the energy differences of s- cis and s- trans conformations of OC – NR–CH 2 may be small.…”
Section: Resultsmentioning
confidence: 92%
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“…They also reported that treatment of 22 with FeCl 3 underwent intramolecular reactions to give chlorinated γ-lactone with loss of stereochemistry on the side chain . The difference in stability can be explained, similar to the cyclization of other ethenetricarboxylate derivatives. , Triester 22 may be more stable in s- cis conformation of OC – O–CH 2 as shown in Scheme , probably because of the steric repulsion. In diester amide A (in Scheme ), the energy differences of s- cis and s- trans conformations of OC – NR–CH 2 may be small.…”
Section: Resultsmentioning
confidence: 92%
“… 2-Alkenyl amides of ethenetricarboxylates also undergo facile intramolecular ene reactions (part b) . In addition, reaction of 1,1-diethyl 2-hydrogen ethenetricarboxylate 1 and 2-furylmethylamines in the presence of EDCI/HOBt/Et 3 N at room temperature led directly to intramolecular Diels–Alder adducts (part c) …”
Section: Introductionmentioning
confidence: 99%
“…Although this approach has been known for a long time and has been systematically studied, it remains limited in terms of substrate scope. For example, activating groups, such as halogens on the furan ring ,,, or electron-withdrawing groups attached to the olefin, ,, are often necessary for good reactivity. The cycloaddition reactions of unactivated substrates are reversible; even sterically unhindered substrates with a monosubstituted terminal olefin can undergo a retro-Diels–Alder reaction to regenerate the starting material .…”
Section: Introductionmentioning
confidence: 80%
“…We recently became interested in an alternative approach for one-step synthesis of these structures: intramolecular furan Diels–Alder reactions of N -allyl- N -furfurylamides to afford oxygen-bridged hexahydroisoindoles (Figure b). The oxygen bridge and the olefin group of these products offer handles for further elaboration. Although this approach has been known for a long time and has been systematically studied, it remains limited in terms of substrate scope.…”
Section: Introductionmentioning
confidence: 99%