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Beilstein J. Org. Chem. 2014, 10, 2539–2549, doi:10.3762/bjoc.10.265
Graphical Abstract
Figure 1: Structure of N-acyl homoserine lactone (AHL) and putative n→π* interaction. Attenuation of n→π* int...
Scheme 1: Synthesis of natural AHLs 3a–f.
Scheme 2: Synthesis of brominated AHLs 6a-f and iodinated AHLs 8a–f (#commercially available compound).
Scheme 3: Synthesis of chlorinated AHL analogues 11a–f.
Figure 2: Normalized fluorescence values for natural AHLs 3a,b and α-haloacylated analogues 6, 8 and 11 teste...
Figure 3: Proposed models (Chem3D Pro) of N-(2R)- (left) and N-(2S)-chlorohexanoyl-(S)-homoserine lactone (ri...
Beilstein J. Org. Chem. 2012, 8, 2124–2131, doi:10.3762/bjoc.8.239
Figure 1: DPP inhibitors.
Scheme 1: Synthesis of chiral α-chloro-N-p-toluenesulfinylaldimines 3.
Scheme 2: Synthesis of (SS,2S,3S)-γ-chloro-α,β-diaminocarboxylamides 5. aYield in parentheses results from th...
Figure 2: Crystal structure of syn-γ-chloro-α,β-diaminocarboxylamide syn-5b.
Scheme 3: Transition-state model for reaction of the Z-enolate of glycinamides 4 in the Mannich-type addition...
Scheme 4: Synthesis of N-sulfinyl-β,γ-aziridino-α-amino carboxylic amides 8.
Scheme 5: α-Deprotection and subsequent ring-closure of syn-γ-chloro-α,β-diamino carboxylic amides syn-5.
Scheme 6: N-p-toluenesulfinyl-deprotection of syn-γ-chloro-α,β-diaminocarboxylamides syn-5.