Acyclic Remote 1,5- and 1,4,5-Stereocontrol in the Catalytic Stereoselective Reactions of β-Lactams with Aldehydes: The Effect of the N-Methylimidazole Ligand.
Plata, Paulina; Klimczak, Urszula; Zambroń, Bartosz K; The Journal of organic chemistry 83 (2018) 14527–14552; doi:10.1021/acs.joc.8b02333

data_4035682
_publ_section_title
;
 Acyclic Remote 1,5- and 1,4,5-Stereocontrol in the Catalytic
 Stereoselective Reactions of \b-Lactams with Aldehydes: The Effect of the
 N-Methylimidazole Ligand.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14527
_journal_page_last               14552
_journal_paper_doi               10.1021/acs.joc.8b02333
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H34 O5 Si'
_chemical_formula_sum            'C18 H34 O5 Si'
_chemical_formula_weight         358.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 96.127(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0101(6)
_cell_length_b                   8.1359(7)
_cell_length_c                   33.077(2)
_cell_measurement_reflns_used    2940
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      60.17
_cell_measurement_theta_min      4.03
_cell_volume                     2143.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.712
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_Laue_measured_fraction_full 0.712
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24104
_diffrn_reflns_point_group_measured_fraction_full 0.708
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         60.169
_diffrn_reflns_theta_min         4.032
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_T_max  0.8360
_exptl_absorpt_correction_T_min  0.5520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.499
_exptl_crystal_size_min          0.162
_refine_diff_density_max         1.004
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.23(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         4491
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1686
_refine_ls_R_factor_gt           0.1221
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1496P)^2^+13.9562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3039
_refine_ls_wR_factor_ref         0.3319
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.703
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                2940
_reflns_number_total             4491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02333_si_005.cif
_cod_data_source_block           BZ_G382_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035682
_shelx_estimated_absorpt_t_min   0.552
_shelx_estimated_absorpt_t_max   0.836
_shelxl_version_number           2014-3
_shelx_res_checksum              86650
_shelx_hkl_checksum              51996