Additives Promote Noyori-type Reductions of a β-Keto-γ-lactam: Asymmetric Syntheses of Serotonin Norepinephrine Reuptake Inhibitors
Nicholas A. Magnus; Bret A. Astleford; Dana L. T. Laird; Todd D. Maloney; Adam D. McFarland; John R. Rizzo; J. Craig Ruble; Gregory A. Stephenson; James P. Wepsiec; Journal of Organic Chemistry 78 (2013) 5768–5774; doi:10.1021/jo400589j

data_4028298
_publ_section_title
;
 Additives Promote Noyori-type Reductions of a \b-Keto-\g-lactam:
 Asymmetric Syntheses of Serotonin Norepinephrine Reuptake Inhibitors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5768
_journal_page_last               5774
_journal_paper_doi               10.1021/jo400589j
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C37 H45 Cl2 N O10 S'
_chemical_formula_weight         766.70
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.099(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9176(5)
_cell_length_b                   13.8269(7)
_cell_length_c                   14.4534(7)
_cell_measurement_reflns_used    8067
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.57
_cell_measurement_theta_min      3.13
_cell_volume                     1937.96(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16499
_diffrn_reflns_theta_full        64.99
_diffrn_reflns_theta_max         64.99
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    2.479
_exptl_absorpt_correction_T_max  0.8861
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Sheldrick, G. M.: SADABS, Bruker AXS area detector scaling and absorption, 
version 2008/1, University of G\"ottingen, Germany 2008.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       tabular
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(16)
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5816
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0971P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                5144
_reflns_number_total             5816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400589j_si_001.cif
_cod_data_source_block           08037_0m
_cod_database_code               4028298