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_4025592
_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_sum            'C19 H28 O2'
_chemical_formula_weight         288.41
_chemical_name_common
;
(1S,5S,2E)-1-Cyclohexyl-7-phenylhept-2-ene-1,5-diol
;
_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                   6.149(3)
_cell_length_b                   9.052(3)
_cell_length_c                   30.88(2)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      14
_cell_volume                     1718.8(15)
_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 0.958
_diffrn_measured_fraction_theta_max 0.958
_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  0.1446
_diffrn_reflns_av_sigmaI/netI    0.1044
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            2549
_diffrn_reflns_theta_full        57.47
_diffrn_reflns_theta_max         57.47
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        10
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(13)
_refine_ls_extinction_coef       0.0117(13)
_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   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1678
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+4.0670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2463
_reflns_number_gt                980
_reflns_number_total             2110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1008959_si_002.cif
_cod_data_source_block           s1628rc
_cod_original_cell_volume        1719.0(15)
_cod_database_code               4025592