1
526
Helvetica Chimica Acta ± Vol. 87 (2004)
Experimental Part
General. All solvents and reagents were commercially available and used as received. Thin-layer
chromatography (TLC): silica gel F254 (pre-coated plates), visualization under UV light. Flash-column
1
13
chromatography (FC): silica gel (100 ± 200 mesh). H- and C-NMR spectra: at 400 and 100 MHz, resp.,
chemical shifts d referenced to internal solvent signals. All compounds were fully characterized by TLC, GC, FT-
1
13
IR, H- and C-NMR, GC-MS (Agilent 6890N ± 5973N; HP-5MS), and MS.
General Procedure for Aqueous Aza-Type Michael Addition Reactions. To a transition-metal-salt catalyst
(
(
0.1 mmol, 0.1 equiv.) in H
1.2 mmol), and the mixture was stirred for 15 ± 24 h at r.t. Then, the mixture was extracted with CH
SO ), filtered, and evaporated. The resulting crude product was purified by
2
O (3 ml) were added the a,b-unsaturated electrophile (1 mmol) and the amine
2
2
Cl , and the
combined org. layers were dried (Na
FC (SiO ).
2
4
2
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Received February 16, 2004