Highly diastereoselective and enantioselective Michael addition of 5H-oxazol-4-ones to ?,?-unsaturated ketones catalyzed by a new bifunctional organocatalyst with broad substrate scope and applicability
Huicai Huang; Kailong Zhu; Wenbin Wu; Zhichao Jin; Jinxing Ye; Chem.Commun. 48 (2012) 461–; doi:10.1039/c1cc15928c

data_7107163
_publ_section_title
;
 Highly diastereoselective and enantioselective Michael addition of
 5H-oxazol-4-ones to ?,?-unsaturated ketones catalyzed by a new
 bifunctional organocatalyst with broad substrate scope and applicability
;
_journal_name_full               Chem.Commun.
_journal_page_first              461
_journal_paper_doi               10.1039/c1cc15928c
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H22 Br N O3'
_chemical_formula_weight         428.32
_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                 90.851(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.773(3)
_cell_length_b                   6.0463(13)
_cell_length_c                   13.400(3)
_cell_measurement_reflns_used    3906
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      3.04
_cell_volume                     1034.8(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7395
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.007
_exptl_absorpt_correction_T_max  0.8559
_exptl_absorpt_correction_T_min  0.3890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.155
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0983P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                3639
_reflns_number_total             4172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc15928c.txt
_cod_data_source_block           dm1197
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7107163