Asymmetric Synthesis of Enaminophosphines via Palladacycle-Catalyzed Addition of Ph2PH to α,β-Unsaturated Imines
Yinhua Huang; Renta Jonathan Chew; Sumod A. Pullarkat; Yongxin Li; Pak-Hing Leung; Journal of Organic Chemistry 77 (2012) 6849–6854; doi:10.1021/jo300893s

data_4027377
_publ_section_title
;
 Asymmetric Synthesis of Enaminophosphines via Palladacycle-Catalyzed
 Addition of Ph2PH to \a,\b-Unsaturated Imines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6849
_journal_page_last               6854
_journal_paper_doi               10.1021/jo300893s
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C48 H46 Cl N2 O2 P Pd S, C6 H6'
_chemical_formula_sum            'C54 H52 Cl N2 O2 P Pd S'
_chemical_formula_weight         965.86
_chemical_name_systematic
; 
 ? 
;
_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                   13.8975(5)
_cell_length_b                   15.3683(6)
_cell_length_c                   21.8526(8)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.37
_cell_volume                     4667.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0962
_diffrn_reflns_av_sigmaI/netI    0.1034
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            76243
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.8019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       needle
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.746
_refine_diff_density_min         -1.557
_refine_diff_density_rms         0.213
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         14193
_refine_ls_number_restraints     169
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0681P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                10485
_reflns_number_total             14193
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300893s_si_002.cif
_cod_data_source_block           leung642
_cod_database_code               4027377