Catalytic Enantioselective Synthesis of a cis-β-Boronyl Cyclobutylcarboxyester Scaffold and Its Highly Diastereoselective Nickel/Photoredox Dual-Catalyzed Csp3‒Csp2 Cross-Coupling to Access Elusive trans-β-Aryl/Heteroaryl Cyclobutylcarboxyesters
Nguyen, Kevin; Clement, Helen A.; Bernier, Louise; Coe, Jotham W.; Farrell, William; Helal, Christopher J.; Reese, Matthew R.; Sach, Neal W.; Lee, Jack C.; Hall, Dennis G.; ACS Catalysis  (2020) 404–413; doi:10.1021/acscatal.0c04520

data_4518341
_publ_section_title
;
 Catalytic Enantioselective Synthesis of a cis-\b-Boronyl
 Cyclobutylcarboxyester Scaffold and Its Highly Diastereoselective
 Nickel/Photoredox Dual-Catalyzed Csp3--Csp2 Cross-Coupling to Access
 Elusive trans-\b-Aryl/Heteroaryl Cyclobutylcarboxyesters
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              404
_journal_page_last               413
_journal_paper_doi               10.1021/acscatal.0c04520
_journal_year                    2020
_chemical_formula_moiety         'C12 H14 O2'
_chemical_formula_sum            'C12 H14 O2'
_chemical_formula_weight         190.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 110.663(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.2075(9)
_cell_length_b                   6.9155(4)
_cell_length_c                   20.9784(11)
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.68
_cell_measurement_theta_min      4.51
_cell_volume                     2064.3(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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.443
_diffrn_reflns_theta_min         4.505
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.8985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0612P)^2^+0.6410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1572
_reflns_number_total             2045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04520_si_004.cif
_cod_data_source_block           dgh2003
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4518341
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.937
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              24608
_shelx_hkl_checksum              94846