Organoboron Initiated Rh-Catalyzed Asymmetric Cascade Reactions: A Subtle Switch in Regioselectivity Leading to Chiral 3-Benzazepine Derivatives
Claraz, Aurélie; Serpier, Fabien; Darses, Sylvain; ACS Catalysis 7 (2017) 3410–; doi:10.1021/acscatal.7b00511

data_4514139
_publ_section_title
;
 Organoboron Initiated Rh-Catalyzed Asymmetric Cascade Reactions: A Subtle
 Switch in Regioselectivity Leading to Chiral 3-Benzazepine Derivatives
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              3410
_journal_paper_doi               10.1021/acscatal.7b00511
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H28 N2 O6 S'
_chemical_formula_sum            'C28 H28 N2 O6 S'
_chemical_formula_weight         520.58
_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'
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.808(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.930(2)
_cell_length_b                   11.5659(17)
_cell_length_c                   15.2580(19)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      67.9
_cell_measurement_theta_min      3.77
_cell_volume                     2579.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            54988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.452
_diffrn_reflns_theta_min         3.024
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 3776 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     673
_refine_ls_number_reflns         9358
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.8405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                8663
_reflns_number_total             9358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00511_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4514139
_shelx_shelxl_version_number     2014/7