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Electrospray mass spectrometry for detailed mechanistic studies of a complex organocatalyzed triple cascade reaction

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Alachraf,  M. Wasim
Service Department Schrader (MS), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Handayani,  Peni P.
Service Department Schrader (MS), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Schrader,  Wolfgang
Service Department Schrader (MS), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Alachraf, M. W., Handayani, P. P., Hüttl, M. R. M., Grondal, C., Enders, D., & Schrader, W. (2011). Electrospray mass spectrometry for detailed mechanistic studies of a complex organocatalyzed triple cascade reaction. Organic & Biomolecular Chemistry, 9(4), 1047-1053. doi:10.1039/C003433A.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-C9CE-F
Abstract
The development of modular combinations of organocatalytic reactions into cascades has been shown to be an effective tool despite the fact that the mechanism of such a complex organocatalytic multistep cascade reaction still remains poorly understood. Here the detailed mechanistic studies of a complex organocatalytic triple cascade reaction for the synthesis of tetra-substituted cyclohexene carbaldehydes are reported. The investigation has been carried out using a triple quadrupole mass spectrometer with electrospray ionization. Important intermediates were detected and characterized through MS/MS studies. A detailed formation pathway is presented based on these characterized intermediates, and supporting the proposed mechanism of the formation of the substituted cyclohexene carbaldehydes.