Pd-Catalyzed Asymmetric Allylic Etherizations with Oximes by Chiral Alkene-Phosphine Ligands
Ziping Cao; Zhaoqun Liu; Yilin Liu; Haifeng Du; Journal of Organic Chemistry 76 (2011) 6401–6406; doi:10.1021/jo200925q

data_4026490
_publ_section_title
;
 Pd-Catalyzed Asymmetric Allylic Etherizations with Oximes by Chiral
 Alkene-Phosphine Ligands
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6401
_journal_page_last               6406
_journal_paper_doi               10.1021/jo200925q
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 Cl N O'
_chemical_formula_sum            'C23 H20 Cl N O'
_chemical_formula_weight         361.85
_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                 99.978(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3229(16)
_cell_length_b                   7.8229(12)
_cell_length_c                   11.7671(18)
_cell_measurement_reflns_used    10884
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.12
_cell_volume                     935.9(3)
_computing_cell_refinement       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_collection       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_reduction        'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10856
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    1.880
_exptl_absorpt_correction_T_max  0.4719
_exptl_absorpt_correction_T_min  0.4300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi March, 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.47
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.034(13)
_refine_ls_extinction_coef       0.0193(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0285P)^2^+0.2690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                3153
_reflns_number_total             3360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200925q_si_002.cif
_cod_data_source_block           sx2935
_cod_original_cell_volume        935.9(2)
_cod_database_code               4026490