Chiral pyrrolidines and piperidines from enantioselective rhodium-catalyzed cascade arylative cyclization.
Serpier, Fabien; Flamme, Benjamin; Brayer, Jean-Louis; Folléas, Benoît; Darses, Sylvain; Organic letters 17 (2015) 1720–1723; doi:10.1021/acs.orglett.5b00493

data_1554867
_publ_section_title
;
 Chiral pyrrolidines and piperidines from enantioselective
 rhodium-catalyzed cascade arylative cyclization.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1720
_journal_page_last               1723
_journal_paper_doi               10.1021/acs.orglett.5b00493
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H26 Br N O4 S'
_chemical_formula_sum            'C23 H26 Br N O4 S'
_chemical_formula_weight         492.42
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.237(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8067(14)
_cell_length_b                   9.9678(14)
_cell_length_c                   11.8916(17)
_cell_measurement_reflns_used    9489
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.81
_cell_measurement_theta_min      2.42
_cell_volume                     1126.7(3)
_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    'SHELXS-2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35224
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.120
_diffrn_reflns_theta_min         2.143
_exptl_absorpt_coefficient_mu    1.946
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.667
_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    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2796 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0110(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         6605
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.1142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6251
_reflns_number_total             6605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00493_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554867
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              3918
_shelx_hkl_checksum              12116