Aldol Reaction of N-tert-Butanesulfinyl Imidates under Basic Conditions for Diastereoselective Synthesis of anti-Aldols.
Li, Chun-Tian; Liu, Hui; Xu, Yan-Jun; Lu, Chong-Dao; The Journal of organic chemistry 82 (2017) 11253–11261; doi:10.1021/acs.joc.7b01982

data_4032916
_publ_section_title
;
 Aldol Reaction of N-tert-Butanesulfinyl Imidates under Basic Conditions
 for Diastereoselective Synthesis of anti-Aldols.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11253
_journal_page_last               11261
_journal_paper_doi               10.1021/acs.joc.7b01982
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H29 N O3 S'
_chemical_formula_sum            'C19 H29 N O3 S'
_chemical_formula_weight         351.49
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 109.012(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.935(3)
_cell_length_b                   15.723(4)
_cell_length_c                   12.065(3)
_cell_measurement_reflns_used    1209
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.0717
_cell_measurement_theta_min      2.3577
_cell_volume                     1961.2(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.1161
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9304
_diffrn_reflns_point_group_measured_fraction_full 0.760
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         2.358
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0621 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.8830.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         5247
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0431P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.489
_reflns_Friedel_fraction_full    0.519
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                2775
_reflns_number_total             5247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01982_si_003.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 4032916--4032917.cif.'
_cod_original_cell_volume        1961.2(8)
_cod_database_code               4032916
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              38793
_shelx_hkl_checksum              20024