BINAP-CuH-catalysed enantioselective allylation using alkoxyallenes to access 1,2-<i>syn-tert</i>,<i>sec</i>-diols.
Navaneetha, N.; Maurya, Sundaram; Behera, Prativa; Jadhav, Sandip B.; Magham, Lakshmi Revati; Nanubolu, Jagadeesh Babu; Roy, Lisa; Chegondi, Rambabu; Chemical science 15 (2024) 20379–20387; doi:10.1039/d4sc07002j

data_1573251
_publ_section_title
;
 BINAP-CuH-catalysed enantioselective allylation using alkoxyallenes to
 access 1,2-<i>syn-tert</i>,<i>sec</i>-diols.
;
_journal_issue                   48
_journal_name_full               'Chemical science'
_journal_page_first              20379
_journal_page_last               20387
_journal_paper_doi               10.1039/d4sc07002j
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H26 O3'
_chemical_formula_sum            'C25 H26 O3'
_chemical_formula_weight         374.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-04-21 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.903(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0727(18)
_cell_length_b                   17.381(3)
_cell_length_c                   8.2903(16)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.516
_cell_measurement_theta_min      2.345
_cell_volume                     1028.0(4)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14285
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.907
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_type   multi-scan
_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_density_diffrn    1.210
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/hexane (1:9)'
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4670
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0399P)^2^+0.1090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4304
_reflns_number_total             4670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07002j2.cif
_cod_data_source_block           KB741_0m
_cod_depositor_comments
'Adding full bibliography for 1573250--1573252.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1573251
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              40093
_shelx_hkl_checksum              15419