Reaction of Silyllithium, α-Keto N-tert-Butanesulfinyl Imidates and Aldehydes for Asymmetric Synthesis of α-Substituted β-(Silyloxy)-α-hydroxy Acid Derivatives.
Huang, Wei; Liu, Hui; Xu, Yan-Jun; Lu, Chong-Dao; The Journal of organic chemistry 82 (2017) 10748–10755; doi:10.1021/acs.joc.7b02214

data_4032886
_publ_section_title
;
 Reaction of Silyllithium, \a-Keto N-tert-Butanesulfinyl Imidates and
 Aldehydes for Asymmetric Synthesis of \a-Substituted
 \b-(Silyloxy)-\a-hydroxy Acid Derivatives.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10748
_journal_page_last               10755
_journal_paper_doi               10.1021/acs.joc.7b02214
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H24 N2 O5 S'
_chemical_formula_sum            'C19 H24 N2 O5 S'
_chemical_formula_weight         392.46
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.405(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.812(6)
_cell_length_b                   6.112(3)
_cell_length_c                   14.148(8)
_cell_measurement_reflns_used    1876
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.0239
_cell_measurement_theta_min      2.6168
_cell_volume                     984.7(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4985
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.093
_diffrn_reflns_theta_max         25.093
_diffrn_reflns_theta_min         2.617
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0523 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.8780.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.0657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.778
_reflns_Friedel_fraction_max     0.778
_reflns_number_gt                2690
_reflns_number_total             3145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02214_si_003.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 4032886--4032887.cif.'
_cod_database_code               4032886
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              34835
_shelx_hkl_checksum              21646