Palladium-Catalyzed Synthesis of Enantiomerically Pure α-Substituted Allylboronic Esters and Their Addition to Aldehydes
Enrique Fernández; Jörg Pietruszka; Wolfgang Frey; Journal of Organic Chemistry 75 (2010) 5580–5589; doi:10.1021/jo1008959

data_4025594
_publ_section_title
;
 Palladium-Catalyzed Synthesis of Enantiomerically Pure \a-Substituted
 Allylboronic Esters and Their Addition to Aldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5580
_journal_page_last               5589
_journal_paper_doi               10.1021/jo1008959
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C17 H20 O2'
_chemical_formula_sum            'C17 H20 O2'
_chemical_formula_weight         256.33
_chemical_name_systematic
; 
(1R,5R)-1,5-diphenylpentane-1,5-diol 
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.201(11)
_cell_angle_beta                 76.936(11)
_cell_angle_gamma                90.000(12)
_cell_formula_units_Z            4
_cell_length_a                   11.1451(11)
_cell_length_b                   11.2829(10)
_cell_length_c                   11.9726(16)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19
_cell_measurement_theta_min      12.5
_cell_volume                     1461.2(3)
_computing_cell_refinement       'Siemens Xscans, Release 2.31'
_computing_data_collection       'Siemens Xscans, Release 2.31'
_computing_data_reduction        'Siemens Xscans, Release 2.31'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       Omega-Scan
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0847
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8182
_diffrn_reflns_theta_full        60.00
_diffrn_reflns_theta_max         60.00
_diffrn_reflns_theta_min         3.80
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_coef       0.0054(4)
_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   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     694
_refine_ls_number_reflns         8182
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.2343
_refine_ls_R_factor_gt           0.1079
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+6.0300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2119
_refine_ls_wR_factor_ref         0.2872
_reflns_number_gt                2955
_reflns_number_total             8182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1008959_si_004.cif
_cod_data_source_block           s1590rc
_cod_database_code               4025594