Issue 9, 2012
From the journal:

Organic & Biomolecular Chemistry

Studies of the H–D exchange mechanism of malonganenone B†

Peter G. K. Clark,ab   Matthias Leinac  and  Robert A. Keyzers*ab  

* Corresponding authors

a School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand

b Centre for Biodiscovery, Victoria University of Wellington, PO Box 600, Wellington, New Zealand
E-mail: rob.keyzers@vuw.ac.nz
Fax: +64 4 463 5241
Tel: +64 4 463 5117

c Center for Theoretical Chemistry and Physics, New Zealand Institute for Advanced Study, Massey University Auckland, Private Bag 102904, North Shore City, New Zealand

Abstract

Malonganenone B (1) exhibits an unusual H–D exchange of a formyl proton when in deuteric-NMR solvents. Synthetic and kinetic investigations were made to probe the mechanism of this exchange, which appears to occur via an uncommon and transient amine–amide NHC intermediate.

Graphical abstract: Studies of the H–D exchange mechanism of malonganenone B

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Article information

DOI
https://doi.org/10.1039/C2OB06926A
Article type
Communication
Submitted
15 Nov 2011
Accepted
08 Dec 2011
First published
09 Dec 2011

Org. Biomol. Chem., 2012,10, 1725-1729

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Studies of the H–D exchange mechanism of malonganenone B

P. G. K. Clark, M. Lein and R. A. Keyzers, Org. Biomol. Chem., 2012, 10, 1725 DOI: 10.1039/C2OB06926A

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