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_4032887
_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         'C29 H37 N O5 S Si'
_chemical_formula_sum            'C29 H37 N O5 S Si'
_chemical_formula_weight         539.74
_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                 98.661(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.734(7)
_cell_length_b                   18.450(19)
_cell_length_c                   12.022(12)
_cell_measurement_reflns_used    1060
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.0657
_cell_measurement_theta_min      2.2077
_cell_volume                     1477(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7473
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.003
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_min         2.038
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9073
_exptl_absorpt_correction_T_min  0.8224
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.149
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 871 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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4697
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0303P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.806
_reflns_Friedel_fraction_max     0.806
_reflns_number_gt                2855
_reflns_number_total             4697
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02214_si_002.cif
_cod_data_source_block           5fb
_cod_depositor_comments
'Adding full bibliography for 4032886--4032887.cif.'
_cod_database_code               4032887
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.9073
_shelx_res_checksum              30271
_shelx_hkl_checksum              77596