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J. Nöth, K. J. Frankowski, B. Neuenswander, J. Aubé, O. Reiser, J. Comb. Chem. 2008, 10, 456-459
Web edition: http://dx.doi.org/10.1021/cc700202c
A three-component method for synthesizing highly-substituted γ-lactams from readily available maleimides, aldehydes and amines is described. A new reductive amination/intramolecular lactamization sequence provides a straightforward route to the lactam products in a single manipulation. The general utility of this method is demonstrated by the parallel synthesis of a γ-lactam library.
S. Has-Becker, K. Bodmann, R. Kreuder, G. Santoni, T. Rein, O. Reiser, Synlett 2001, 1395-1398
A new protocol for the alkenylation of carbonyl compounds with phosphonates (Horner-Wadsworth-Emmons reaction) is described: Aldehydes react with phosphonates already at room temperature in the presence of triethylamine without further activation by Lewis-acids if high-pressure (8 kbar) is applied to the system. Based on this protocol a domino process was developed combining the HWE reaction with a Michael reaction, thus allowing the one-pot synthesis of β-amino esters, β-thio esters or β-thio nitriles.
R. Räcker, K. Döring, O. Reiser, J. Org. Chem. 2000, 65, 6932-6939
Web edition: http://dx.doi.org/10.102/jo0004916
A new method for the synthesis of [1,4]oxazepin-7-ones from readily available aldehydes and -amino alcohols was developed using the Baylis-Hillman reaction as the key step. To determine the scope and limitations of the method, a mixture library was synthesized from six aldehydes and six -amino alcohols on the soluble polymer support poly(ethylene glycol) 5000 monomethyl ether (MeOPEG) via split synthesis and analyzed by GC-EIMS. Those oxazepines that were formed predominantly were resynthesized in a parallel synthesis and fully characterized. Thus, we have shown that split synthesis on MeOPEG can be an efficient method to rapidly screen the substrate spectrum of a newly developed reaction sequence.
Peter Kreitmeier - 04.07.2011 07:33
