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Structures of the Reactive Intermediates in Organocatalysis with Diarylprolinol Ethers by Uroš Grošelj; Dieter Seebach; D. Michael Badine; W. Bernd Schweizer; Albert K. Beck; Ingo Krossing; Petra Klose; Yujiro Hayashi; Tadafumi Uchimaru is a Chemistry article available to read on EtoBox.

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## Abstract Structures of the reactive intermediates (enamines and iminium ions) of organocatalysis with diarylprolinol derivatives have been determined. To this end, diarylprolinol methyl and silyl ethers, 1, and aldehydes, PhCH~2~CHO, ^__t__^BuCH~2~CHO, PhCH=CHCHO, are condensed to the corresponding enamines, A and 3 (__Scheme 2__), and cinnamoylidene iminium salts, B and 4 (__Scheme 3__). These are isolated and fully characterized by melting/decomposition points, [__α__]~D~, elemental analysis, IR and NMR spectroscopy, and high‐resolution mass spectrometry (HR‐MS). Salts with BF~4~, PF~6~, SbF~6~, and the __weakly coordinating__ Al[OC(CF~3~)~3~]~4~ anion were prepared. X‐Ray crystal structures of an enamine and of six iminium salts have been obtained and are described herein (__Figs. 2__ and __4–8__, and __Tables 2__ and __7__) and in a previous preliminary communication (__Helv. Chim. Acta__ 2008, __91__, 1999). According to the NMR spectra (in CDCl~3~, (D~6~)DMSO, (D~6~)acetone, or CD~3~OD; __Table 1__), the major isomers 4 of the iminium salts have (__E__)‐configuration of the exocyclic NC(1′) bond, but there are up to 11% of the (__Z__)‐isomer present in these solutio

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Author

Uroš Grošelj; Dieter Seebach; D. Michael Badine; W. Bernd Schweizer; Albert K. Beck; Ingo Krossing; Petra Klose; Yujiro Hayashi; Tadafumi Uchimaru

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

2009

Language

EN

Field

Chemistry (Physical Sciences)