Direct Asymmetric Aldol Reaction of 5H-Oxazol-4-ones with Aldehydes Catalyzed by Chiral Guanidines
Tomonori Misaki; Gouta Takimoto; Takashi Sugimura; Journal of the American Chemical Society 132 (2010) 6286–6287; doi:10.1021/ja101216x

data_4102391
_publ_section_title
;
 Direct Asymmetric Aldol Reaction of 5H-Oxazol-4-ones with Aldehydes
 Catalyzed by Chiral Guanidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6286
_journal_page_last               6287
_journal_paper_doi               10.1021/ja101216x
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H18 Br N O4 '
_chemical_formula_sum            'C16 H18 Br N O4'
_chemical_formula_weight         368.23
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.4681(17)
_cell_length_b                   12.7255(16)
_cell_length_c                   17.4475(18)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    292.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.0
_cell_volume                     1658.1(5)
_computing_cell_refinement       'Rigaku Diffractometer Controller'
_computing_data_collection       'Rigaku Diffractometer Controller'
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      292.1
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.077
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12854
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_exptl_absorpt_coefficient_mu    2.503
_exptl_absorpt_correction_T_max  1.2650
_exptl_absorpt_correction_T_min  0.4992
_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    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.75
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1506 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       314(28)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     219
_refine_ls_number_reflns         1951
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    8.6143    -4.3360    6.1533
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0620
_reflns_number_gt                1951
_reflns_number_total             3670
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja101216x_si_001.cif
_cod_data_source_block           '_misaki1'
_cod_original_formula_sum        'C16 H18 Br N O4 '
_cod_database_code               4102391