Access to Polyfunctionalized Chiral Piperidines through Enantioselective Addition-Carbocyclization Cascade Reaction Catalyzed by a Rhodium(I)-Diene Complex.
Serpier, Fabien; Brayer, Jean-Louis; Folléas, Benoît; Darses, Sylvain; Organic letters 17 (2015) 5496–5499; doi:10.1021/acs.orglett.5b02858

data_1555421
_publ_section_title
;
 Access to Polyfunctionalized Chiral Piperidines through Enantioselective
 Addition-Carbocyclization Cascade Reaction Catalyzed by a
 Rhodium(I)-Diene Complex.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5496
_journal_page_last               5499
_journal_paper_doi               10.1021/acs.orglett.5b02858
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C24 H31 N O5 S'
_chemical_formula_sum            'C24 H31 N O5 S'
_chemical_formula_weight         445.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8376(2)
_cell_length_b                   10.6992(4)
_cell_length_c                   37.5454(14)
_cell_measurement_reflns_used    1849
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      52.12
_cell_measurement_theta_min      4.76
_cell_volume                     2345.00(15)
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            10505
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        58.903
_diffrn_reflns_theta_max         58.903
_diffrn_reflns_theta_min         4.297
_exptl_absorpt_coefficient_mu    1.508
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.549
_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    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0436P)^2^+0.2607P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.871
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                2412
_reflns_number_total             3142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02858_si_001.cif
_cod_data_source_block           shelx
_cod_database_code               1555421
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              11740
_shelx_hkl_checksum              3271