Catalytic asymmetric P<sup>(III)</sup>-additions to salicylaldehydes enable divergent stereoselective dearomatizations of phenols.
Clarkson, Aidan J.; Alley, Kimberly A.; Werley, Bryn K.; Robins, Jacob G.; Liu, Shubin; Johnson, Jeffrey S.; Chemical science 17 (2026) 2837–2846; doi:10.1039/d5sc08571c

data_1576731
_publ_section_title
;
 Catalytic asymmetric P<sup>(III)</sup>-additions to salicylaldehydes
 enable divergent stereoselective dearomatizations of phenols.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              2837
_journal_page_last               2846
_journal_paper_doi               10.1039/d5sc08571c
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C24 H29.00 Br1 N1 O9 P1'
_chemical_formula_sum            'C24 H29 Br N O9 P'
_chemical_formula_weight         586.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2025-03-14
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_audit_update_record
;
2025-07-23 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.924(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0691(5)
_cell_length_b                   26.0181(12)
_cell_length_c                   11.5610(6)
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    150
_cell_measurement_theta_max      133
_cell_measurement_theta_min      7
_cell_volume                     2530.7(2)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.112
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            87412
_diffrn_reflns_theta_full        66.790
_diffrn_reflns_theta_max         66.790
_diffrn_reflns_theta_min         3.397
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.282
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1208.000
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.49
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4457
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.0008124
_refine_ls_shift/su_mean         0.0000246
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 4.33P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1056
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1056
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3666
_reflns_number_total             4479
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0518
_oxford_refine_ls_scale          0.4265(6)
_oxford_reflns_number_all        4457
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 'cu_24299_a.res in P2(1)/c'
_cod_data_source_file            d5sc08571c2.cif
_cod_data_source_block           24299
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C24 H29.00 Br1 N1 O9 P1'
_cod_database_code               1576731