Kinetic Resolution of Chiral Cyclohex-2-enones by Rhodium(I)/binap-Catalyzed 1,2- and 1,4-Additions.
Kolb, Andreas; Hirner, Sebastian; Harms, Klaus; Zezschwitz, Paultheo von; Organic letters 14 (2012) 1978–1981; doi:10.1021/ol300387f

data_1507575
_publ_section_title
;
 Kinetic Resolution of Chiral Cyclohex-2-enones by
 Rhodium(I)/binap-Catalyzed 1,2- and 1,4-Additions.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1978
_journal_page_last               1981
_journal_paper_doi               10.1021/ol300387f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C13 H16 O'
_chemical_formula_sum            'C13 H16 O'
_chemical_formula_weight         188.26
_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                   5.7228(4)
_cell_length_b                   9.7296(5)
_cell_length_c                   19.3240(14)
_cell_measurement_reflns_used    7237
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.1
_cell_volume                     1075.97(12)
_computing_cell_refinement       'STOE WinCell (X-Area)'
_computing_data_collection       'STOE WinXpose (X-Area)'
_computing_data_reduction        'STOE WinIntegrate (X-Area)'
_computing_molecular_graphics    'Diamond 3.2'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2008 (Giacovazzo et al, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0763
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9155
_diffrn_reflns_theta_full        25.13
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0431P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                1138
_reflns_number_total             1355
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol300387f_si_002.cif
_cod_data_source_block           ak391-s
_cod_database_code               1507575