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24 Analytical data for the modified salen ligand (1R,2R)-7: mp 89-93 °C; [α]D
29 -329.5 (c 1.0, CHCl3); IR (KBr): 2963, 2875, 1628, 1597, 1445, 1263, 699 cm-1; 1H NMR (200 MHz, CDCl3): δ = 13.13 (s, OH, 2 H), 8.00 (s, CHN, 2 H), 7.45 (d, J = 1.8 Hz, 2 H), 7.25-7.09 (m, 10 H), 6.92 (d, J = 1.8 Hz, 2 H), 3.13-2.99 (m, 2 H), 2.50-2.25 (m, 4 H), 2.12-1.94 (m, 4 H), 1.86-1.69 (m, 4 H), 1.66-1.44 (m, 2 H), 1.30 (s, 18 H), 0.60 (t, J = 7.2 Hz, 6 H), 0.53 (t, J = 7.2 Hz, 6 H); 13C NMR (50 MHz, CDCl3): δ = 165.5 (2 × CHN), 157.5 (2 × C), 148.5 (2 × C), 139.2 (2 × C), 133.1 (2 × C), 129.2 (2 × CH), 127.2 (4 × CH), 127.0 (4 × CH), 125.8 (2 × CH), 124.7 (2 × CH), 117.5 (2 × C), 72.3 (2 × CH), 49.0 (2 × C), 34.0 (2 × C), 32.9 (2 × CH2), 31.5 (6 × CH3), 28.0 (2 × CH2), 27.1 (2 × CH2), 24.3 (2 × CH2), 8.7 (4 × CH3); Anal. Calcd for C50H66N2O2: C, 82.60; H, 9.15; N, 3.85. Found: C, 82.55; H, 9.23; N, 3.83; HRMS: [M + Na]+ calcd for C50H66N2O2Na: 749.5022, found: 749.5021.
25 Analytical data for the complex (1R,2R)-8: [α]D
29 -1420
(c 0.01, CHCl3); IR (KBr): 3429, 2961, 2873, 1622, 1533, 1437, 1258, 700, 546 cm-1; HRMS: [M - Cl]+ calcd for C50H64N2O2Cr: 776.4373, found: 776.4392.
26
General Procedure for High-Pressure Allylation: In a 2-mL Teflon ampoule were placed catalyst 1g (8.7 mg, 1 mol%), CH2Cl2 (ca. 1 mL), followed by aldehyde (1 mmol) and allyltributyltin (1.1-1.2 equiv). Finally, the ampoule was filled with CH2Cl2, closed and placed in a high-pressure vessel, and the pressure was slowly increased to 10 kbar at 20 °C. After the pressure had stabilized, the reaction mixture was kept under these conditions for 24 h. After decompression, the reaction mixture was diluted with wet Et2O and dried over MgSO4. After evaporation of solvents, the residue was chromatographed on a silica gel column (hexane-EtOAc).
27 The enantioselectivity of homoallylic alcohols 3a-f was determined by GC employing a capillary chiral β-dex 120 column. Alcohol 3f was analyzed directly, 3a, 3c and 3d as their O-trimethylsilyl derivatives, 3b as an acetate and 3e as a trifluoroacetate.