A highly stereoselective sequential allylic transfer reaction of diene with diboronyl reagent and aldehydes promoted by nickel catalyst.
Yu, Chan-Mo; Youn, Jinsuop; Yoon, Seok-Keun; Hong, Young-Tack; Organic letters 7 (2005) 4507–4510; doi:10.1021/ol051806c

data_1506717
_publ_section_title
;
 A highly stereoselective sequential allylic transfer reaction of diene
 with diboronyl reagent and aldehydes promoted by nickel catalyst.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4507
_journal_page_last               4510
_journal_paper_doi               10.1021/ol051806c
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C22 H27 N O4 S'
_chemical_formula_weight         401.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.49(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.108(4)
_cell_length_b                   27.256(12)
_cell_length_c                   12.829(5)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.83
_cell_measurement_theta_min      2.97
_cell_volume                     2131.8(19)
_computing_cell_refinement       'XSCANS (Siemens, 1995)'
_computing_data_collection       'XSCANS (Siemens, 1995)'
_computing_data_reduction        'SHELXTL (Siemens, 1997)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1997)'
_computing_publication_material  'SHELXTL (Siemens, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3085
_diffrn_reflns_theta_full        22.49
_diffrn_reflns_theta_max         22.49
_diffrn_reflns_theta_min         1.76
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.2783
_exptl_absorpt_correction_T_min  0.2550
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            'colorless         '
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block             '
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0037(8)
_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   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.2087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1072
_reflns_number_gt                1826
_reflns_number_total             2783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051806csi20050829_081921.cif
_cod_data_source_block           1152
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               1506717