Copper-Hydride-Catalyzed Enantioselective Processes with Allenyl Boronates. Mechanistic Nuances, Scope, and Utility in Target-Oriented Synthesis.
Sun, Yu; Zhou, Yuebiao; Shi, Ying; Del Pozo, Juan; Torker, Sebastian; Hoveyda, Amir H.; Journal of the American Chemical Society 141 (2019) 12087–12099; doi:10.1021/jacs.9b05465

data_4128547
_publ_section_title
;
 Copper-Hydride-Catalyzed Enantioselective Processes with Allenyl
 Boronates. Mechanistic Nuances, Scope, and Utility in Target-Oriented
 Synthesis.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12087
_journal_page_last               12099
_journal_paper_doi               10.1021/jacs.9b05465
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         '(C36 H52 B Cu N2 O2), 1/2(C4 H10 O)'
_chemical_formula_sum            'C38 H57 B Cu N2 O2.5'
_chemical_formula_weight         656.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 107.96(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            4
_cell_length_a                   10.458(2)
_cell_length_b                   25.050(5)
_cell_length_c                   15.770(3)
_cell_measurement_reflns_used    9624
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.58
_cell_measurement_theta_min      3.43
_cell_volume                     3930.0(15)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.801
_diffrn_reflns_theta_min         3.434
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2016). TWINABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             1412
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         14191
_refine_ls_number_restraints     503
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+0.7621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12706
_reflns_number_total             14191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05465_si_002.cif
_cod_data_source_block           C36H52BCuN2O2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        3929.9(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C38 H57 B Cu N2 O2.50'
_cod_database_code               4128547
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.639
_shelx_estimated_absorpt_t_max   0.932
_shelx_res_checksum              54978
_shelx_hkl_checksum              67718