Efficient synthesis of α-quaternary α-hydroxy-β-amino esters via silyl glyoxylate-mediated three-component reactions.
Jiang, Jiu-Long; Yao, Ming; Lu, Chong-Dao; Organic letters 16 (2014) 318–321; doi:10.1021/ol403388w

data_1513545
_publ_section_title
;
 Efficient synthesis of \a-quaternary \a-hydroxy-\b-amino esters via silyl
 glyoxylate-mediated three-component reactions.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              318
_journal_page_last               321
_journal_paper_doi               10.1021/ol403388w
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H28 Br N O4 S'
_chemical_formula_sum            'C18 H28 Br N O4 S'
_chemical_formula_weight         434.38
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.496(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.8785(17)
_cell_length_b                   18.843(5)
_cell_length_c                   9.875(3)
_cell_measurement_reflns_used    3028
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.20
_cell_measurement_theta_min      2.16
_cell_volume                     1088.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0866
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13393
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.003
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.037(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1513
_reflns_number_gt                2399
_reflns_number_total             3807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403388w_si_003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1513545