Enantioselective organocatalytic asymmetric allylic alkylation. Bis(phenylsulfonyl)methane addition to MBH carbonates.
Companyó, Xavier; Valero, Guillem; Ceban, Victor; Calvet, Teresa; Font-Bardía, Mercé; Moyano, Albert; Rios, Ramon; Organic & biomolecular chemistry 9 (2011) 7986–7989; doi:10.1039/c1ob06308a

data_7152094
_publ_section_title
;
 Enantioselective organocatalytic asymmetric allylic alkylation.
 Bis(phenylsulfonyl)methane addition to MBH carbonates.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7986
_journal_page_last               7989
_journal_paper_doi               10.1039/c1ob06308a
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C24 H22 O6 S2'
_chemical_formula_sum            'C24 H22 O6 S2'
_chemical_formula_weight         470.54
_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                   5.919(3)
_cell_length_b                   14.531(5)
_cell_length_c                   25.735(11)
_cell_measurement_reflns_used    185
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     2213.4(17)
_computing_cell_refinement       'AUTOMAR (Claudio Klein, 2007)'
_computing_data_collection       'MARXDS (Claudio Klein, 2005)'
_computing_data_reduction        'MARSCALE (Claudio Klein, 2007)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      105(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.809
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi scan'
_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  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            16387
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.35
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(13)
_refine_ls_extinction_coef       0.016(2)
_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   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0779
_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^)+(0.0785P)^2^+5.2849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.2035
_reflns_number_gt                5116
_reflns_number_total             5891
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06308a.txt
_cod_data_source_block           xcpm80
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7152094