Direct Catalytic Asymmetric Addition of Allyl Cyanide to Ketones via Soft Lewis Acid/Hard Brønsted Base/Hard Lewis Base Catalysis
Ryo Yazaki; Naoya Kumagai; Masakatsu Shibasaki; Journal of the American Chemical Society 132 (2010) 5522–5531; doi:10.1021/ja101687p

data_4102285
_publ_section_title
;
 Direct Catalytic Asymmetric Addition of Allyl Cyanide to Ketones via Soft
 Lewis Acid/Hard Br\/onsted Base/Hard Lewis Base Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5522
_journal_page_last               5531
_journal_paper_doi               10.1021/ja101687p
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C68 H72 Cl2 Cu2 P4 '
_chemical_formula_sum            'C68 H72 Cl2 Cu2 P4'
_chemical_formula_weight         1211.21
_space_group_IT_number           178
_symmetry_cell_setting           hexagonal
_symmetry_Int_Tables_number      178
_symmetry_space_group_name_Hall  'P 61 2 (0 0 5)'
_symmetry_space_group_name_H-M   'P 61 2 2'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_formula_units_Z            18
_cell_length_a                   22.9187(5)
_cell_length_b                   22.9187(5)
_cell_length_c                   61.6463(12)
_cell_measurement_reflns_used    111013
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      33.4
_cell_measurement_theta_min      3.1
_cell_volume                     28042.6(10)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.090
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            143521
_diffrn_reflns_theta_full        33.39
_diffrn_reflns_theta_max         33.39
_exptl_absorpt_coefficient_mu    2.895
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             11376.00
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.24
_refine_diff_density_min         -0.36
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1366 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.629
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     374
_refine_ls_number_reflns         3478
_refine_ls_R_factor_gt           0.1176
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3420
_reflns_number_gt                3071
_reflns_number_total             3478
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja101687p_si_001.cif
_cod_data_source_block           '_091028-2'
_cod_original_sg_symbol_Hall     'P 61 2 (0 0 -1)'
_cod_original_formula_sum        'C68 H72 Cl2 Cu2 P4 '
_cod_database_code               4102285