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_1576730
_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_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 N1 O7 P1'
_chemical_formula_sum            'C22 H24 N O7 P'
_chemical_formula_weight         445.41
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2025-02-08
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0600(2)
_cell_length_b                   11.8513(4)
_cell_length_c                   26.1740(8)
_cell_measurement_reflns_used    9694
_cell_measurement_temperature    150
_cell_measurement_theta_max      132
_cell_measurement_theta_min      7
_cell_volume                     2189.98(12)
_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    'SIR92 (Altomare et al., 1994)'
_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       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            75568
_diffrn_reflns_theta_full        66.762
_diffrn_reflns_theta_max         66.762
_diffrn_reflns_theta_min         3.377
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.493
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.35
_refine_ls_abs_structure_details 'Flack (1983), 1630 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.0004346
_refine_ls_shift/su_mean         0.0000300
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 1.67P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1479
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1479
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                3210
_reflns_number_total             3885
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.78
_oxford_diffrn_Wilson_scale      61.98
_oxford_refine_ls_r_factor_ref   0.0650
_oxford_refine_ls_scale          0.13179(9)
_oxford_reflns_number_all        3868
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 'cu_25036 in P2(1)2(1)2(1)'
_cod_data_source_file            d5sc08571c2.cif
_cod_data_source_block           25036
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C22 H24 N1 O7 P1'
_cod_database_code               1576730