Organocatalytic asymmetric synthesis of α-amino esters from sulfoxonium ylides
Guo, Wengang; Wang, Min; Han, Zhengyu; Huang, Hai; Sun, Jianwei; Chemical Science  (2021) –; doi:10.1039/D1SC02439F

data_1564261
_publ_section_title
;
 Organocatalytic asymmetric synthesis of \a-amino esters from sulfoxonium
 ylides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02439F
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_chemical_name_systematic
'Phenyl (S)-2-((4-methoxyphenyl)amino)-2-phenylacetate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-29 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.888(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2280(4)
_cell_length_b                   7.9448(2)
_cell_length_c                   10.7105(2)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    99.93(17)
_cell_measurement_theta_max      72.3690
_cell_measurement_theta_min      4.3790
_cell_volume                     1715.00(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.93(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     80.00 173.00   1.00   10.00    --  104.18  30.00 -90.00   93
  2  \w   -109.00 -15.00   1.00    4.00    --  -40.20 -37.00-120.00   94
  3  \w    -64.00  30.00   1.00    4.00    --  -40.20  37.00  60.00   94
  4  \w    -20.00  73.00   1.00    4.00    --   40.20 -77.00 150.00   93
  5  \w     31.00 102.00   1.00   10.00    --  104.18-111.00 -30.00   71
  6  \w     26.00 109.00   1.00   10.00    --  104.18-111.00-180.00   83
  7  \w    108.00 153.00   1.00   10.00    --  104.18  77.00-180.00   45
  8  \w     34.00 122.00   1.00   10.00    --  104.18 -61.00-180.00   88
  9  \w     20.00 106.00   1.00   10.00    --  104.18 -94.00  30.00   86
 10  \w     47.00 132.00   1.00   10.00    --  104.18 -45.00   0.00   85
 11  \w     76.00 168.00   1.00   10.00    --  104.18  61.00 -30.00   92
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0175825000
_diffrn_orient_matrix_UB_12      0.1887513000
_diffrn_orient_matrix_UB_13      0.0073933000
_diffrn_orient_matrix_UB_21      0.0733810000
_diffrn_orient_matrix_UB_22      -0.0449773000
_diffrn_orient_matrix_UB_23      0.0346077000
_diffrn_orient_matrix_UB_31      0.0122647000
_diffrn_orient_matrix_UB_32      -0.0011369000
_diffrn_orient_matrix_UB_33      -0.1398500000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4868
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.565
_diffrn_reflns_theta_min         4.143
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0331P)^2^+0.5582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                2924
_reflns_number_total             3026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02439f2.cif
_cod_data_source_block           wguo5cult
_cod_database_code               1564261
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.966
_diffrn_oxdiff_digest_frames
;
01b48b6497bb50c5924c95c4e8d1f8f79b00027e33e
;
_diffrn_oxdiff_digest_hkl
;
015a54516616a3b9c9604bd0f9139bb51b0d70
;
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C22(H22), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              9347
_shelx_hkl_checksum              57380
_olex2_date_sample_data_collection 2020-10-23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.877