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1 article(s) from Schnell, Anne

Mechanistic studies of an L-proline-catalyzed pyridazine formation involving a Diels–Alder reaction with inverse electron demand

Anne Schnell,
J. Alexander Willms,
S. Nozinovic and
Marianne Engeser

Beilstein J. Org. Chem. 2019, 15, 30–43, doi:10.3762/bjoc.15.3

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Graphical Abstract

Figure 1: Charge-tagged L-proline-derived catalyst 1∙Cl [18].

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Scheme 1: Putative catalytic cycle [51] for the L-proline-catalyzed Diels–Alder reaction with inverse electron de...

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Scheme 2: Synthesis of the charge-tagged tetrazine 4∙Br as a reactant for the proline-catalyzed Diels–Alder r...

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Scheme 3: Reaction R1: L-proline-catalyzed reaction between 2 and acetone.

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Figure 2: NMR monitoring of reaction R1 in deuterated DMSO (concentration of tetrazine 0.005 mmol/mL).

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Scheme 4: Equilibrium of oxazolidinone and enamine formation.

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Figure 3: a) ESI mass spectrum of reaction R1 after 26 min. b) ESIMS monitoring of reaction R1. To better vis...

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Figure 4: ESI mass spectrum of reaction R1 with preformed I₁ 8 minutes after adding substrate 2.

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Scheme 5: Reaction R2: L-proline-catalyzed reaction between charge-tagged substrate 4∙Br and acetone. The reg...

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Figure 5: ESI mass spectrum of reaction R2 using a continuous-flow setup with a calculated reaction time of 8...

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Figure 6: a) Reaction R2 after two hours (syringe setup). b) ESIMS monitoring of reaction R2. Signal intensit...

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Scheme 6: Reaction R3: substrate 2, acetone and charge-tagged catalyst 1∙Cl.

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Figure 7: ESI mass spectrum of reaction R3 at 60 °C after 1.5 h.

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Scheme 7: General catalytic cycle for reactions R1–R3.

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Figure 8: ESIMS monitoring of reaction R3. The plotted intensity values for each molecule are a sum of all co...

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Figure 9: Isomeric forms in equilibrium: enamine [I_3a]⁺, oxazolidinone [I_3b]⁺ and iminium [I_3c]⁺.

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Figure 10: ESI(+) CID spectrum of mass-selected [I₃]⁺ (m/z 353); collision energy voltage 1 V.

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Figure 11: ESI(+) CID spectrum of mass selected [II₃]⁺ (m/z 589); collision energy voltage 5 V.

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Figure 12: ESI(+) CID spectrum of mass selected [III₃]⁺ (m/z 561); collision energy voltage 10 V.

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Published 03 Jan 2019

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