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

2011 ◽  
Vol 9 (4) ◽  
pp. 1047-1053 ◽  
Author(s):  
M. Wasim Alachraf ◽  
Peni P. Handayani ◽  
Matthias R. M. Hüttl ◽  
Christoph Grondal ◽  
Dieter Enders ◽  
...  
2014 ◽  
Vol 10 ◽  
pp. 2027-2037 ◽  
Author(s):  
J Alexander Willms ◽  
Rita Beel ◽  
Martin L Schmidt ◽  
Christian Mundt ◽  
Marianne Engeser

A new 4-hydroxy-L-proline derivative with a charged 1-ethylpyridinium-4-phenoxy substituent has been synthesized with the aim of facilitating mechanistic studies of proline-catalyzed reactions by ESI mass spectrometry. The charged residue ensures a strongly enhanced ESI response compared to neutral unmodified proline. The connection by a rigid linker fixes the position of the charge tag far away from the catalytic center in order to avoid unwanted interactions. The use of a charged catalyst leads to significantly enhanced ESI signal abundances for every catalyst-derived species which are the ones of highest interest present in a reacting solution. The new charged proline catalyst has been tested in the direct asymmetric inverse aldol reaction between aldehydes and diethyl ketomalonate. Two intermediates in accordance with the List–Houk mechanism for enamine catalysis have been detected and characterized by gas-phase fragmentation. In addition, their temporal evolution has been followed using a microreactor continuous-flow technique.


1998 ◽  
Author(s):  
Rebecca A. Clewell ◽  
Wayne T. Brashear ◽  
David T. Tsui ◽  
Sanwat Chaudhuri ◽  
Rachel S. Cassady

FEBS Letters ◽  
1996 ◽  
Vol 389 (3) ◽  
pp. 309-313 ◽  
Author(s):  
Monica Di Luca ◽  
Lucia Pastorino ◽  
Vittorio Raverdino ◽  
Pierre N.E. De Graan ◽  
Antonio Caputi ◽  
...  

Lab on a Chip ◽  
2005 ◽  
Vol 5 (8) ◽  
pp. 869 ◽  
Author(s):  
Yanou Yang ◽  
Chen Li ◽  
Jun Kameoka ◽  
Kelvin H. Lee ◽  
H. G. Craighead

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