8839for 1 h. The reaction mixture was quenched with ca. 5 mL of cold water, and the solvent was removed by rotary evaporation. The residue was dissolved in EtOAc (50 mL), washed with water (3 X 50 mL) and brine (50 mL), dried over MgSO,, filtered, and evaporated to afford 0.80 g (96%) of 12b as a brown oil, which solidified upon evacuation: 'H NMR (d, J = 8.9 Hz, 1 H), 7.86 (d, J = 8.6 Hz, 1 H), 7.62 (d, J = 1.6 Hz, I H), 7.32 (dd, J = 2.2, 8.9 Hz, 1 H), 5.56 (s, 2 H), 3.60 (s, 3 H), 2.38 (s, 3 HI.Methoxymethyl CLHydroxy-2-naphthoate (12c). A solution of acetoxy ester 12b (0.65 g, 2.37 mmol) in a mixture of 40 mL of MeOH, 7 mL of saturated aqueous NaHCO,, and 7 mL of H 2 0 was stirred at room temperature for 6 h. The reaction mixture was quenched with I N HCI (ca. IO mL) to afford a tan precipitate. MeOH was removed by rotary evaporation, and the solid was isolated by rapid filtration. The solid was dissolved in EtOAc (50 mL), and the solution was washed with brine, dried over MgS04, filtered, and concentrated to afford 0.57 g (97%) of 12c as a tan solid: mp 130-1 32 OC; 'H NMR (300 MHz, CDCI,) 6 8.58 (s, 1 H), 8.05 (dd, J = 1.6, 8.6 Hz, 1 H), 7.80 (d, J = 8.6 Hz, 1 H), 7.72 (d, J = 8.6 Hz, 1 H), 7.17 (m, 2 H), 5.55 (s, 2 H), 5.49 (s, 1 H), 3.60 (s, 3 H); HRMS m / z [(M -H)'] calcd 231.0657, obsd 231.0658.Kinetics Studies. The reaction of imide esters 1Od and 10h with amine 9 in the presence and absence of templates l l a and l l b was performed in CHCI, solution containing ca. 4 equiv of Et,N. A Waters 600 HPLC equipped with a UV detector (254 nm) was used for the analysis of reaction mixtures. Analyses were performed with a mixture of watermethanol-Et,N (30:70:0.1) as the mobile phase and a reverse-phase column (Beckman CIS column, Ultrasphere ODS dp, 5 pm, 4.6 mm i.d. X 25 cm, flow rate = 1.5 mL/min). The integrations and concentrations of all the peaks were calculated on an NEC computer with Waters 820 Baseline software. In case of prolonged reactions (>IO0 min), a methanol flush was performed between injections to ensure complete elution of esters 1Od and 10h. CHCl, was dried over molecular sieves or by passage through Al20, before use. All experiments were performed at (300 MHz, CDCI,) d 8.65 (s, 1 H), 8.1 1 (dd, J = 1.6, 8.7 Hz, 1 H), 7.99 ambient temperature (21.5-23.0 "C). Each run was performed 2-4 times to obtain average values for the data.Calibration of HPLC. The HPLC was calibrated by the injection of solutions of amine 9 and template l l a of varying concentration. A linear relationship between concentration and peak area was observed. Reaction mixtures were analyzed on the basis of either the area of the template peak or the rario of the amine and template peaks.Reaction Procedures. During initial studies (data presented in Figures 1 and 5), reactions were performed in 100 pL of solvent in I-mL. Wheaton serum vials equipped with aluminum caps and Teflon-coated silicone septa (procedure A). During subsequent studies (data presented in Figures 2-4), I-mL Wheaton screw-cap vials equipped with Minine...