Compound 3b
(1S,2S,3S,3aS,6aR)-1-benzoyl-1'-methyl-3-phenyl-3,3a-dihydro-1H-spiro[pentalene-2,3'-pyrrolo[2,3-b]pyridine]-2',4(1'H,6aH)-dione
From: Switchable regioselectivity in amine-catalysed asymmetric cycloadditions
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Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
The title compound was prepared according to the general procedure for asymmetric γ,β’-regioselective [6 + 2] cycloaddition as outlined in the synthesis of 3a. 3b, white solid, 20.3 mg, 48% yield; [α]D20 = -16.8 (c = 0.56 in CHCl3); 97% e.e., determined by HPLC analysis [Daicel chiralpak AD, n-hexane/i-PrOH = 60/40, 1.0 mL/min, λ = 254 nm, t (major) = 9.10 min, t (minor) = 13.47 min]; 1H NMR (600 MHz, CDCl3): δ (ppm) 7.93 (d, J = 4.8 Hz, 1H), 7.74 (dd, J = 6.0 Hz, 2.4 Hz, 1H), 7.52 (d, J = 7.2 Hz, 1H), 7.43 (t, J = 7.2 Hz, 1H), 7.31 (d, J = 7.2 Hz, 2H), 7.27 (m, 2H), 7.03-7.00 (m, 3H), 6.92-6.89 (m, 3H), 6.20 (dd, J = 6.0 Hz, 1.8 Hz, 1H), 4.90 (m, 1H), 4.41 (d, J = 7.8 Hz, 1H), 3.92 (d, J = 12.0 Hz,, 1H), 3.68 (dd, J = 12.0 Hz, 7.2 Hz, 1H), 2.58 (s, 3H); 13C NMR (150 MHz, CDCl3): δ (ppm) 207.5, 197.6, 175.7, 163.9, 155.7, 147.4, 136.6, 133.5, 133.1, 133.0, 132.3, 128.3, 128.0, 127.9, 127.8, 127.8, 120.4, 117.7, 67.1, 56.9, 55.9, 51.3, 47.2, 24.8; ESI-HRMS: calcd. for C28H22N2O3+Na+ 457.1523, found 457.1528.