Rhodium-Catalyzed Asymmetric 1,4-Addition of α,β-Unsaturated Imino Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands.
Lee, Ansoo; Kim, Hyunwoo; Journal of the American Chemical Society 137 (2015) 11250–11253; doi:10.1021/jacs.5b07034

data_4129498
_publ_section_title
;
 Rhodium-Catalyzed Asymmetric 1,4-Addition of \a,\b-Unsaturated Imino
 Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11250
_journal_page_last               11253
_journal_paper_doi               10.1021/jacs.5b07034
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 N O2 P'
_chemical_formula_sum            'C23 H20 N O2 P'
_chemical_formula_weight         373.37
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.0398(5)
_cell_length_b                   9.0398(5)
_cell_length_c                   39.2730(19)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.59
_cell_volume                     2779.3(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            18224
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.602
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1638 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.006(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0356P)^2^+0.5844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.833
_reflns_number_gt                3664
_reflns_number_total             3797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b07034_si_003.cif
_cod_data_source_block           d13207
_cod_database_code               4129498
_shelx_estimated_absorpt_t_min   0.904
_shelx_estimated_absorpt_t_max   0.949
_shelxl_version_number           2013-3
_shelx_res_checksum              81523
_shelx_hkl_checksum              77278