Chemo- and diastereoselective tandem dual oxidation of B(pin)-substituted allylic alcohols: synthesis of B(pin)-substituted epoxy alcohols, 2-keto-anti-1,3-diols and dihydroxy-tetrahydrofuran-3-ones
Hussain, Nusrah; Hussain, Mahmud M.; Carroll, Patrick J.; Walsh, Patrick J.; Chemical Science 4 (2013) 3946–; doi:10.1039/c3sc51616d

data_1514544
_publ_section_title
;
 Chemo- and diastereoselective tandem dual oxidation of B(pin)-substituted
 allylic alcohols: synthesis of B(pin)-substituted epoxy alcohols,
 2-keto-anti-1,3-diols and dihydroxy-tetrahydrofuran-3-ones
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              3946
_journal_paper_doi               10.1039/c3sc51616d
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_sum            'C19 H20 Cl2 O4'
_chemical_formula_weight         383.25
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_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                   7.8057(5)
_cell_length_b                   10.1854(7)
_cell_length_c                   23.4262(17)
_cell_measurement_temperature    143(1)
_cell_volume                     1862.5(2)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega 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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31652
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.64(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0828P)^2^+1.3825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1540
_reflns_number_gt                3085
_reflns_number_total             3408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc51616d.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1514544