Catalytic Enantioselective Allyl- and Crotylboration of Aldehydes Using Chiral Diol.SnCl4 Complexes. Optimization, Substrate Scope and Mechanistic Investigations
Vivek Rauniyar; Huimin Zhai; Dennis G. Hall; Journal of the American Chemical Society 130 (2008) 8481–8490; doi:10.1021/ja8016076

data_4107960
_publ_section_title
;
 Catalytic Enantioselective Allyl- and Crotylboration of Aldehydes Using
 Chiral Diol.SnCl4 Complexes. Optimization, Substrate Scope and
 Mechanistic Investigations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8481
_journal_page_last               8490
_journal_paper_doi               10.1021/ja8016076
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C30 H46 Cl4 O2 Sn, C7 H8, H2 O'
_chemical_formula_sum            'C37 H56 Cl4 O3 Sn'
_chemical_formula_weight         809.31
_chemical_name_systematic
;

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;
_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                   9.9594(7)
_cell_length_b                   12.2807(8)
_cell_length_c                   31.266(2)
_cell_measurement_reflns_used    6722
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.15
_cell_volume                     3824.1(4)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF-96 (Beurskens et al., 1996)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            33714
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_T_max  0.9083
_exptl_absorpt_correction_T_min  0.5724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       prism
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         8736
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+1.4331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                8210
_reflns_number_total             8736
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja8016076-file004.cif
_cod_data_source_block           dgh0807
_cod_database_code               4107960