Cr(III)(salen)Cl Catalyzed Enantioselective Intramolecular Addition of Tertiary Enamides to Ketones: A General Access to Enantioenriched 1H-Pyrrol-2(3H)-one Derivatives Bearing a Hydroxylated Quaternary Carbon Atom
Luo Yang; De-Xian Wang; Zhi-Tang Huang; Mei-Xiang Wang; Journal of the American Chemical Society 131 (2009) 10390–10391; doi:10.1021/ja904534t

data_4104790
_publ_section_title
;
 Cr(III)(salen)Cl Catalyzed Enantioselective Intramolecular Addition of
 Tertiary Enamides to Ketones: A General Access to Enantioenriched
 1H-Pyrrol-2(3H)-one Derivatives Bearing a Hydroxylated Quaternary Carbon
 Atom
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10390
_journal_page_last               10391
_journal_paper_doi               10.1021/ja904534t
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C24 H20 Br N O2'
_chemical_formula_sum            'C24 H20 Br N O2'
_chemical_formula_weight         434.32
_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                 104.63(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4421(17)
_cell_length_b                   10.189(2)
_cell_length_c                   12.446(3)
_cell_measurement_reflns_used    4724
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.49
_cell_volume                     1035.9(4)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 1990)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1352
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4724
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    2.003
_exptl_absorpt_correction_T_max  0.6670
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.038(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.651
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4724
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.651
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0586
_reflns_number_gt                2880
_reflns_number_total             4724
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja904534t_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        1035.8(4)
_cod_database_code               4104790