Enantioselective Synthesis of α-Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols
Yamamoto, Kosuke; Ishimaru, Shota; Oyama, Tatsuya; Tanigawa, Satoko; Kuriyama, Masami; Onomura, Osamu; Organic Process Research & Development 23 (2019) 660–; doi:10.1021/acs.oprd.8b00407

data_1554185
_publ_section_title
;
 Enantioselective Synthesis of \a-Substituted Serine Derivatives via
 Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols
;
_journal_issue                   4
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              660
_journal_paper_doi               10.1021/acs.oprd.8b00407
_journal_volume                  23
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C34 H40 N2 O7 S'
_chemical_formula_sum            'C34 H40 N2 O7 S'
_chemical_formula_weight         620.76
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.263(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.240(5)
_cell_length_b                   14.762(4)
_cell_length_c                   16.651(5)
_cell_measurement_reflns_used    10108
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.90
_cell_volume                     3342.5(18)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27799
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.156
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320.00
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.39
_refine_ls_abs_structure_details
;
 Flack x determined using 3234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     799
_refine_ls_number_reflns         15166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0491P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                11629
_reflns_number_total             15166
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            op8b00407_si_002.cif
_cod_data_source_block           1780c
_cod_database_code               1554185
_shelx_res_checksum              13310
_shelx_hkl_checksum              39930