syntheses of pyrrolidine, piperidine, and related heterocycles have been well-explored. The use of versatile tethers in intramolecular aza-Michael chemistry has received less attention; such reactions are particularly powerful because they remove the constraint of needing a pre-existing C-N bond in the molecule to forge a new one. For reaction optimization (Table ), we chose substrates that could be prepared in three steps from commercially available 3-[(tert-butyldimethylsilyl)oxy]-1-propanal in a sequence of HWE olefination, TBS removal, and sulfamoylation. Treatment of A with 10-CSA, (S)-BINOL phosphoric acid, or quinine resulted in low yields of desired cyclized product B (Table , Entries 1-3). Phosphines are strong promoters of Michael reactions. Using 1 equivalent of PEt3 with catalytic (S)-BINOL phosphoric acid gave B in an increased yield of 45% (Table , Entry 4). Our laboratory has developed biphasic basic conditions for the ring-opening of epoxides and aziridines by sulfamates ; these conditions were only marginally successful here (Table , Entry 5). The most successful results came from switching to either TBAF or 1,1,3,3-tetramethylguanidine (TMG) in CH2Cl2 or PhCl (Table , Entries 6-9). The reaction could be made catalytic with respect to TMG, but the time had to be extended to 48 hours for full consumption of starting material (Table , Entry 10).