Kinetic resolution of 1-(1-alkynyl)cyclopropyl ketones by gold(I)-catalyzed asymmetric [4+3]cycloaddition with nitrones: scope, mechanism and applications
Yanqing Zhang; Junliang Zhang; Chem.Commun. 48 (2012) 4710–; doi:10.1039/c2cc30309d

data_7107630
_publ_section_title
;
 Kinetic resolution of 1-(1-alkynyl)cyclopropyl ketones by
 gold(I)-catalyzed asymmetric [4+3]cycloaddition with nitrones: scope,
 mechanism and applications
;
_journal_name_full               Chem.Commun.
_journal_page_first              4710
_journal_paper_doi               10.1039/c2cc30309d
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C19 H15 Br O'
_chemical_formula_weight         339.22
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3417(12)
_cell_length_b                   9.098(2)
_cell_length_c                   32.164(7)
_cell_measurement_temperature    296(2)
_cell_volume                     1563.1(6)
_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_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  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            14433
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    2.626
_exptl_absorpt_correction_T_max  0.9301
_exptl_absorpt_correction_T_min  0.5563
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0175P)^2^+0.4436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                1914
_reflns_number_total             2761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc30309d.txt
_cod_data_source_block           (1R,_2S)-1j
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7107630