Enantioselective synthesis of chiral oxazolines from unactivated ketones and isocyanoacetate esters by synergistic silver/organocatalysis.
Martínez-Pardo, Pablo; Blay, Gonzalo; Muñoz, M Carmen; Pedro, José R; Sanz-Marco, Amparo; Vila, Carlos; Chemical communications (Cambridge, England) 54 (2018) 2862–2865; doi:10.1039/c8cc00856f

data_7121304
_publ_section_title
;
 Enantioselective synthesis of chiral oxazolines from unactivated ketones
 and isocyanoacetate esters by synergistic silver/organocatalysis.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2862
_journal_page_last               2865
_journal_paper_doi               10.1039/c8cc00856f
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H40 Br2 N2 O8'
_chemical_formula_weight         716.46
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-01-19 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.082(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8799(2)
_cell_length_b                   29.0285(9)
_cell_length_c                   9.8495(3)
_cell_measurement_reflns_used    1832
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      19.0040
_cell_measurement_theta_min      3.5020
_cell_volume                     1649.81(9)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.1676
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13710
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         3.511
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical absorption correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         7265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1728
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0003P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.774
_reflns_Friedel_fraction_max     0.610
_reflns_number_gt                3368
_reflns_number_total             7265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00856f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7121304.cif.'
_cod_original_cell_volume        1649.83(9)
_cod_database_code               7121304
_shelx_estimated_absorpt_t_min   0.788
_shelx_estimated_absorpt_t_max   0.906
_shelxl_version_number           2014-1
_shelx_res_checksum              54738