2022
DOI: 10.1039/d1qo01688a
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Catalytic properties of 4,5-bridged proline methano- and ethanologues in the Hajos–Parrish intramolecular aldol reaction

Abstract: The catalysis of the Hajos–Parrish reaction by cis- and trans-4,5-ethano-proline was explored experimentally and computationally with DFT (ωB97X-D and MN15) and DLPNO-CCSD(T).

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Cited by 3 publications
(2 citation statements)
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“…The Gibbs free energy of all intermediate compounds, the rate constant (k) and the half-life (t 1/2 ) of the reaction were calculated, respectively. [47][48][49][50][51] As shown in Fig. 5, MPD-O undergoing intramolecular nucleophilic addition to form TS1 through Int1 was the same step for both pathways A and B.…”
Section: Resultsmentioning
confidence: 85%
“…The Gibbs free energy of all intermediate compounds, the rate constant (k) and the half-life (t 1/2 ) of the reaction were calculated, respectively. [47][48][49][50][51] As shown in Fig. 5, MPD-O undergoing intramolecular nucleophilic addition to form TS1 through Int1 was the same step for both pathways A and B.…”
Section: Resultsmentioning
confidence: 85%
“…As an academic, it has been rewarding that cis- and trans- 4,5-methano prolines have rendered valuable service to the development of marketed drugs and to new prototypes that are currently being exploited in ongoing clinical trials many years after publication of our results. Other applications of 4,5-methano L-proline in the context of synthetic methodology, catalysis, and PP2 type helical oligomers have been reported from our group.…”
Section: Medicinal Chemistry-inspired Collaborations With Industry Ma...mentioning
confidence: 80%