BINAPHANE-Catalyzed Asymmetric Synthesis of trans-β-Lactams from Disubstituted Ketenes and N-Tosyl Arylimines.
Chen, Shi; Salo, Eric C.; Wheeler, Kraig A.; Kerrigan, Nessan J.; Organic letters 14 (2012) 1784–1787; doi:10.1021/ol3003783

data_1507572
_publ_section_title
;
 BINAPHANE-Catalyzed Asymmetric Synthesis of trans-\b-Lactams from
 Disubstituted Ketenes and N-Tosyl Arylimines.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1784
_journal_page_last               1787
_journal_paper_doi               10.1021/ol3003783
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C24 H23 N O4 S'
_chemical_formula_sum            'C24 H23 N O4 S'
_chemical_formula_weight         421.49
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 117.639(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.7677(6)
_cell_length_b                   9.8927(3)
_cell_length_c                   20.9508(8)
_cell_measurement_reflns_used    5351
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.466
_cell_measurement_theta_min      4.340
_cell_volume                     4180.4(2)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0856
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16214
_diffrn_reflns_theta_full        67.32
_diffrn_reflns_theta_max         67.32
_diffrn_reflns_theta_min         4.38
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_T_max  0.8723
_exptl_absorpt_correction_T_min  0.5104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent lath'
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+5.5632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                2575
_reflns_number_total             3705
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3003783_si_003.cif
_cod_data_source_block           nker03
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1507572