Synthesis of quaternary carbon stereocenters by copper-catalyzed asymmetric allylic substitution of allyl phosphates with arylboronates.
Takeda, Momotaro; Takatsu, Keishi; Shintani, Ryo; Hayashi, Tamio; The Journal of organic chemistry 79 (2014) 2354–2367; doi:10.1021/jo500068p

data_4029179
_publ_section_title
;
 Synthesis of quaternary carbon stereocenters by copper-catalyzed
 asymmetric allylic substitution of allyl phosphates with arylboronates.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2354
_journal_page_last               2367
_journal_paper_doi               10.1021/jo500068p
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_sum            'C24 H31 Cl F6 N2 O P'
_chemical_formula_weight         543.93
_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                 100.9045(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2658(2)
_cell_length_b                   14.8585(3)
_cell_length_c                   17.0388(4)
_cell_measurement_temperature    93(2)
_cell_volume                     2552.07(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_sigmaI/netI    0.0997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25869
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.98
_exptl_absorpt_coefficient_mu    2.498
_exptl_absorpt_correction_T_max  0.6350
_exptl_absorpt_correction_T_min  0.5212
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     642
_refine_ls_number_reflns         8634
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1901
_reflns_number_gt                6067
_reflns_number_total             8634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500068p_si_001.cif
_cod_data_source_block           1114yu
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4029179