Intramolecular asymmetric propargylation of esters and imides: C-H functionalisation enables stereocontrolled access to UCS1025A.
Corcoran, James C.; Zhu, Jin; Semenick, Mason A.; Welser, Anna L.; Wang, Yi-Ming; Chemical science 16 (2025) 12879–12884; doi:10.1039/d5sc02523k

data_1574791
_publ_section_title
;
 Intramolecular asymmetric propargylation of esters and imides: C-H
 functionalisation enables stereocontrolled access to UCS1025A.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              12879
_journal_page_last               12884
_journal_paper_doi               10.1039/d5sc02523k
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H27 N O2 Si'
_chemical_formula_weight         437.59
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-04-02 deposited with the CCDC.	2025-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_c                   18.9431(13)
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.43
_cell_volume                     2377.3(3)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon III CPAD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36118
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         2.434
_diffrn_source                   'Bruker Venture Duo ImuS'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes, Acetone'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.252
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_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0316P)^2^+0.3093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4278
_reflns_number_total             4871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02523k2.cif
_cod_data_source_block           mo_Corcoran4_a
_cod_depositor_comments
'Adding full bibliography for 1574791--1574792.cif.'
_cod_database_code               1574791
_shelx_shelxl_version_number     2019/1
_shelx_res_checksum              82886