Highly Z-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines
Tomonori Misaki; Kei Kawano; Takashi Sugimura; Journal of the American Chemical Society 133 (2011) 5695–5697; doi:10.1021/ja200283n

data_4105960
_publ_section_title
;
 Highly Z-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones
 with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5695
_journal_page_last               5697
_journal_paper_doi               10.1021/ja200283n
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 Br N O3'
_chemical_formula_sum            'C20 H24 Br N O3'
_chemical_formula_weight         406.32
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                96.981(6)
_cell_angle_beta                 93.8853(15)
_cell_angle_gamma                99.0089(14)
_cell_formula_units_Z            1
_cell_length_a                   5.0852(6)
_cell_length_b                   5.5751(7)
_cell_length_c                   17.793(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     492.58(12)
_computing_cell_refinement       'Rigaku Diffractometer Controller'
_computing_data_collection       'Rigaku Diffractometer Controller'
_computing_data_reduction        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.889
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type  'Quantum CCD1 on Rigaku AFC-7R'
_diffrn_measurement_method       PHIOMEGA
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4169
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.110
_exptl_absorpt_correction_T_max  1.1349
_exptl_absorpt_correction_T_min  0.5022
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor - empirical Absorption Correction, 
Rigaku Corporation, Tokyo, Japan. 
;
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       platelet
_exptl_crystal_F_000             210.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.708
_refine_diff_density_min         -1.110
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1096 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.019(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     251
_refine_ls_number_reflns         2641
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
    Chebychev polynomial with 4 parameters (Carruthers & Watkin, 1979)
    10.8027    -7.1947    5.8227    -3.1555
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0589
_reflns_number_gt                2641
_reflns_number_total             3107
_reflns_threshold_expression     F>2.0\s(F)
_cod_data_source_file            ja200283n_si_002.cif
_cod_data_source_block           22-KK-18
_cod_original_cell_volume        492.57(12)
_cod_database_code               4105960