Design, Synthesis, and Applications of Potential Substitutes of t-Bu-Phosphinooxazoline in Pd-Catalyzed Asymmetric Transformations and Their Use for the Improvement of the Enantioselectivity in the Pd-Catalyzed Allylation Reaction of Fluorinated Allyl Enol Carbonates
Étienne Bélanger; Marie-France Pouliot; Marc-André Courtemanche; Jean-François Paquin; Journal of Organic Chemistry 77 (2012) 317–331; doi:10.1021/jo2019653

data_4026846
_publ_contact_author_address
;
      D\'epartement de Chimie
      Pavillon Alexandre-Vachon, Local 1421
      Universit\'e Laval
      Qu\'ebec, Canada
      G1K 7P4
;
_publ_contact_author_email       jean-francois.paquin@chm.ulaval.ca
_publ_contact_author_fax         418-656-7916
_publ_contact_author_name        'Jean-Fran\,cois Paquin'
_publ_contact_author_phone       '418 656-2131'
_publ_section_title
;
 Design, Synthesis, and Applications of Potential Substitutes of
 t-Bu-Phosphinooxazoline in Pd-Catalyzed Asymmetric Transformations and
 Their Use for the Improvement of the Enantioselectivity in the
 Pd-Catalyzed Allylation Reaction of Fluorinated Allyl Enol Carbonates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              317
_journal_page_last               331
_journal_paper_doi               10.1021/jo2019653
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H30 Cl2 N O P Pd'
_chemical_formula_sum            'C27 H30 Cl2 N O P Pd'
_chemical_formula_weight         592.79
_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                   8.9649(6)
_cell_length_b                   10.4999(7)
_cell_length_c                   27.225(2)
_cell_measurement_reflns_used    9758
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.75
_cell_measurement_theta_min      3.25
_cell_volume                     2562.7(3)
_computing_cell_refinement       'APEX 2 (Bruker, 2005b)'
_computing_data_collection       'APEX 2 (Bruker, 2005b)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            169938
_diffrn_reflns_theta_full        71.24
_diffrn_reflns_theta_max         71.24
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    8.504
_exptl_absorpt_correction_T_max  0.4835
_exptl_absorpt_correction_T_min  0.3823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       Block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.027(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0164
_refine_ls_R_factor_gt           0.0164
_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^)+(0.0298P)^2^+0.9789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0451
_reflns_number_gt                4927
_reflns_number_total             4929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2019653_si_002.cif
_cod_data_source_block           paqum1
_cod_database_code               4026846