Catalytic Enantioselective C-C Bond-Forming Reactions of Deconjugated Butyrolactams: Michael Addition to α,β-Unsaturated Aldehydes and Ketones.
Singha Roy, Soumya Jyoti; Mukherjee, Santanu; The Journal of organic chemistry 83 (2018) 12071–12085; doi:10.1021/acs.joc.8b02051

data_4035203
_publ_section_title
;
 Catalytic Enantioselective C-C Bond-Forming Reactions of Deconjugated
 Butyrolactams: Michael Addition to \a,\b-Unsaturated Aldehydes and
 Ketones.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12071
_journal_page_last               12085
_journal_paper_doi               10.1021/acs.joc.8b02051
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_sum            'C23 H25 Cl N5 O4'
_chemical_formula_weight         470.93
_chemical_name_systematic        2014/7
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 107.337(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.087(4)
_cell_length_b                   8.8775(15)
_cell_length_c                   11.5808(19)
_cell_measurement_reflns_used    5838
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      3.27
_cell_measurement_theta_min      27.02
_cell_volume                     2363.8(7)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34469
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.228
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1423 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.5554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3503
_reflns_number_total             4169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02051_si_005.cif
_cod_data_source_block           14
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4035203
_shelx_estimated_absorpt_t_min   0.507
_shelx_estimated_absorpt_t_max   0.906
_shelxl_version_number           2013-4
_shelx_res_checksum              84648
_shelx_hkl_checksum              11822