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Data for Compound 19: [α]D
20 -76.8 (c 1.45, CHCl3). IR (film): νmax = 3058, 2928, 1446, 1317, 1145, 1086, 801 cm-1. 1H NMR (200 MHz, CDCl3): δ = 1.26 (m, 1 H, 3-Hα), 1.73 (dt, 1 H, J = 8.8, 4.4 Hz, 3-Hβ), 2.20 (m, 1 H, 2-H), 3.11 (ddd, 1 H, J = 4.4, 7.2, 9.2 Hz, 1-H), 6.33 (d, 1 H, J = 15.0 Hz, 2′-H), 6.46 (dd, 1 H, J = 9.2, 14.6 Hz, 1′-H), 7.10-7.61 (m, 13 H, Ar-), 7.84 (m, 2 H, H
ortho
, -SO2Ph). 13C NMR (50 MHz, CDCl3): δ = 19.8 (C-3), 26.1 (C-2), 46.3 (C-1), 127.4-129.1 (CH-Ar), 130.0 (C-2′), 133.1
(C
para
, -SO2Ph), 136.3 and 139.4 (C
ipso
, -Ph), 141.0 (C
ipso
, -SO2Ph), 148.1 (C-1′), 168.7 (CPh2). MS: m/z (%) = 388 (30) [MH+], 307 (15), 246 (35), 154 (100), 77 (55). HMRS: m/z calcd for C24H22NSO2: 388.1371; found: 388.1321 [MH+].
<A NAME="RD21704ST-17">17</A>
The molecular modeling studies were carried out with Maestro v. 5.1.016 coupled to
MacroModel v. 8.1.031, both supplied by Schrodinger, Inc. of Portland, OR, USA. Starting
structures were built by sketching and were atom-typed automatically and energy-minimized
using up to 5000 iterations of TNCG minimization to default convergence. The conformational
search was carried out using the MCMM/Lowmode mixed method, with default settings
based upon the automated setup procedure within Maestro. The conformational constraints
were added manually and set to 25, 100 or 400 kJ/mol in three separate runs for each
of the four models (cis- and trans-cyclopropane, and torsional constraint set to 0 or 180 degrees). The number of trials
was set to 100 since at this value all the low-energy conformations were found at
least 4 times. Minimizations were all achieved with up to 5000 iterations of TNCG
optimization to default convergence, and all structures were successfully converged.
