Nickel-Catalyzed Asymmetric Alkene Hydrogenation of α,β-Unsaturated Esters: High-Throughput Experimentation-Enabled Reaction Discovery, Optimization, and Mechanistic Elucidation.
Shevlin, Michael; Friedfeld, Max R.; Sheng, Huaming; Pierson, Nicholas A.; Hoyt, Jordan M.; Campeau, Louis-Charles; Chirik, Paul J.; Journal of the American Chemical Society 138 (2016) 3562–3569; doi:10.1021/jacs.6b00519

data_4130119
_publ_section_title
;
 Nickel-Catalyzed Asymmetric Alkene Hydrogenation of \a,\b-Unsaturated
 Esters: High-Throughput Experimentation-Enabled Reaction Discovery,
 Optimization, and Mechanistic Elucidation.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3562
_journal_page_last               3569
_journal_paper_doi               10.1021/jacs.6b00519
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C34 H44 F2 Ni O4 P2'
_chemical_formula_weight         675.34
_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
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   14.283(5)
_cell_length_b                   14.834(5)
_cell_length_c                   16.192(5)
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.43
_cell_measurement_theta_min      2.75
_cell_volume                     3431(2)
_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 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0461
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            82559
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         39.499
_diffrn_reflns_theta_min         2.345
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 BRUKER ASX'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       octahedron
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.841
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.245
_refine_diff_density_max         1.363
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.000(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         20539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.1912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                16155
_reflns_number_total             20539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b00519_si_001.cif
_cod_data_source_block           shelx
_cod_database_code               4130119
_shelxl_version_number           2014-3
_shelx_res_checksum              47103
_shelx_hkl_checksum              25265